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molecular formula C4H6O6<br>C4H6O6<br>COOH(CHOH)2COOH B1591660 (2R,3S)-2,3-Dihydroxysuccinic acid hydrate CAS No. 5990-63-6

(2R,3S)-2,3-Dihydroxysuccinic acid hydrate

Cat. No. B1591660
M. Wt: 150.09 g/mol
InChI Key: FEWJPZIEWOKRBE-XIXRPRMCSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US04066772

Procedure details

10.2 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one are converted into the (+)-2,3-dihydroxybutanedioate salt in 100 parts of water at reflux temperature. The solution is treated for 10 minutes with a mixture of 0.5 parts of activated charcoal and 0.2 parts of hyflo. The latter is filtered off over hyflo and the filtrate is cooled till an oily precipitate is formed. The oily product solidifies upon heating for a while. The whole is allowed to cool to room temperature and stirred for 3 hours at this temperature. The product is filtered off, washed with water and dried in vacuo for 18 hours at 60° C, yielding 10.24 parts (85.3%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemi-[R-(R*,R*)](+)-2,3-dihydroxybutanedioate hydrate; mp. 184.1° C; [α] = + 5.13° (c = 1% CH3OH).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH:31][CH:32]([CH:36]([OH:40])[C:37]([O-:39])=[O:38])[C:33]([O-:35])=[O:34].C>O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH2:31].[OH:31][CH:32]([CH:36]([OH:40])[C:37]([OH:39])=[O:38])[C:33]([OH:35])=[O:34] |f:5.6|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OC(C(=O)[O-])C(C(=O)[O-])O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 3 hours at this temperature
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
at reflux temperature
FILTRATION
Type
FILTRATION
Details
The latter is filtered off over hyflo
TEMPERATURE
Type
TEMPERATURE
Details
the filtrate is cooled till an oily precipitate
CUSTOM
Type
CUSTOM
Details
is formed
TEMPERATURE
Type
TEMPERATURE
Details
upon heating for a while
FILTRATION
Type
FILTRATION
Details
The product is filtered off
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried in vacuo for 18 hours at 60° C
Duration
18 h

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
Name
Type
product
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85.3%
Name
Type
product
Smiles
O.OC(C(=O)O)C(C(=O)O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04066772

Procedure details

10.2 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one are converted into the (+)-2,3-dihydroxybutanedioate salt in 100 parts of water at reflux temperature. The solution is treated for 10 minutes with a mixture of 0.5 parts of activated charcoal and 0.2 parts of hyflo. The latter is filtered off over hyflo and the filtrate is cooled till an oily precipitate is formed. The oily product solidifies upon heating for a while. The whole is allowed to cool to room temperature and stirred for 3 hours at this temperature. The product is filtered off, washed with water and dried in vacuo for 18 hours at 60° C, yielding 10.24 parts (85.3%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemi-[R-(R*,R*)](+)-2,3-dihydroxybutanedioate hydrate; mp. 184.1° C; [α] = + 5.13° (c = 1% CH3OH).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH:31][CH:32]([CH:36]([OH:40])[C:37]([O-:39])=[O:38])[C:33]([O-:35])=[O:34].C>O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH2:31].[OH:31][CH:32]([CH:36]([OH:40])[C:37]([OH:39])=[O:38])[C:33]([OH:35])=[O:34] |f:5.6|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OC(C(=O)[O-])C(C(=O)[O-])O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 3 hours at this temperature
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
at reflux temperature
FILTRATION
Type
FILTRATION
Details
The latter is filtered off over hyflo
TEMPERATURE
Type
TEMPERATURE
Details
the filtrate is cooled till an oily precipitate
CUSTOM
Type
CUSTOM
Details
is formed
TEMPERATURE
Type
TEMPERATURE
Details
upon heating for a while
FILTRATION
Type
FILTRATION
Details
The product is filtered off
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried in vacuo for 18 hours at 60° C
Duration
18 h

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
Name
Type
product
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85.3%
Name
Type
product
Smiles
O.OC(C(=O)O)C(C(=O)O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04066772

Procedure details

10.2 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one are converted into the (+)-2,3-dihydroxybutanedioate salt in 100 parts of water at reflux temperature. The solution is treated for 10 minutes with a mixture of 0.5 parts of activated charcoal and 0.2 parts of hyflo. The latter is filtered off over hyflo and the filtrate is cooled till an oily precipitate is formed. The oily product solidifies upon heating for a while. The whole is allowed to cool to room temperature and stirred for 3 hours at this temperature. The product is filtered off, washed with water and dried in vacuo for 18 hours at 60° C, yielding 10.24 parts (85.3%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemi-[R-(R*,R*)](+)-2,3-dihydroxybutanedioate hydrate; mp. 184.1° C; [α] = + 5.13° (c = 1% CH3OH).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH:31][CH:32]([CH:36]([OH:40])[C:37]([O-:39])=[O:38])[C:33]([O-:35])=[O:34].C>O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH2:31].[OH:31][CH:32]([CH:36]([OH:40])[C:37]([OH:39])=[O:38])[C:33]([OH:35])=[O:34] |f:5.6|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OC(C(=O)[O-])C(C(=O)[O-])O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 3 hours at this temperature
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
at reflux temperature
FILTRATION
Type
FILTRATION
Details
The latter is filtered off over hyflo
TEMPERATURE
Type
TEMPERATURE
Details
the filtrate is cooled till an oily precipitate
CUSTOM
Type
CUSTOM
Details
is formed
TEMPERATURE
Type
TEMPERATURE
Details
upon heating for a while
FILTRATION
Type
FILTRATION
Details
The product is filtered off
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried in vacuo for 18 hours at 60° C
Duration
18 h

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
Name
Type
product
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85.3%
Name
Type
product
Smiles
O.OC(C(=O)O)C(C(=O)O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04066772

Procedure details

10.2 parts of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one are converted into the (+)-2,3-dihydroxybutanedioate salt in 100 parts of water at reflux temperature. The solution is treated for 10 minutes with a mixture of 0.5 parts of activated charcoal and 0.2 parts of hyflo. The latter is filtered off over hyflo and the filtrate is cooled till an oily precipitate is formed. The oily product solidifies upon heating for a while. The whole is allowed to cool to room temperature and stirred for 3 hours at this temperature. The product is filtered off, washed with water and dried in vacuo for 18 hours at 60° C, yielding 10.24 parts (85.3%) of 5-chloro-1-{1-[3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one hemi-[R-(R*,R*)](+)-2,3-dihydroxybutanedioate hydrate; mp. 184.1° C; [α] = + 5.13° (c = 1% CH3OH).
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH:31][CH:32]([CH:36]([OH:40])[C:37]([O-:39])=[O:38])[C:33]([O-:35])=[O:34].C>O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20]4=[O:28])[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.[OH2:31].[OH:31][CH:32]([CH:36]([OH:40])[C:37]([OH:39])=[O:38])[C:33]([OH:35])=[O:34] |f:5.6|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
OC(C(=O)[O-])C(C(=O)[O-])O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirred for 3 hours at this temperature
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
at reflux temperature
FILTRATION
Type
FILTRATION
Details
The latter is filtered off over hyflo
TEMPERATURE
Type
TEMPERATURE
Details
the filtrate is cooled till an oily precipitate
CUSTOM
Type
CUSTOM
Details
is formed
TEMPERATURE
Type
TEMPERATURE
Details
upon heating for a while
FILTRATION
Type
FILTRATION
Details
The product is filtered off
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried in vacuo for 18 hours at 60° C
Duration
18 h

Outcomes

Product
Details
Reaction Time
3 h
Name
Type
product
Smiles
Name
Type
product
Smiles
ClC1=CC2=C(N(C(N2)=O)C2CCN(CC2)CCCN2C(NC3=C2C=CC=C3)=O)C=C1
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 85.3%
Name
Type
product
Smiles
O.OC(C(=O)O)C(C(=O)O)O

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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