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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
US04397853

Procedure details

A 46.5 g-quantity of the above compound (free base) is dissolved in 200 ml of ethanol, and a solution of 15 g of L-tartaric acid in 200 ml of water is added to the ethanol solution. The resulting mixture is allowed to stand at room temperature. The crystals thus precipitated are recrystallized three times from ethanol-water (6:4) to give tartrate monohydrate as colorless prisms. The tartrate monohydrate is treated with an aqueous solution of sodium bicarbonate to give (-)-1-[5-(4-fluorophenyl)-4,5-dihydroisoxazol-3-ylmethyl]-4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine. Melting point: 143°-145° C. [α]D25 : -108.8 (chloroform).
Quantity
15 g
Type
reactant
Reaction Step One
Name
ethanol
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
200 mL
Type
solvent
Reaction Step One
Quantity
200 mL
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].FC1C=CC(C2(O)ONC(CN3CCC(N4C5C=CC(Cl)=CC=5NC4=O)CC3)=C2O)=CC=1>C(O)C.O>[OH2:3].[C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7] |f:4.5|

Inputs

Step One
Name
Quantity
15 g
Type
reactant
Smiles
C([C@H](O)[C@@H](O)C(=O)O)(=O)O
Name
ethanol
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=CC=C(C=C1)C1(C(=C(NO1)CN1CCC(CC1)N1C(NC2=C1C=CC(=C2)Cl)=O)O)O
Name
Quantity
200 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
200 mL
Type
solvent
Smiles
C(C)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
to stand at room temperature
CUSTOM
Type
CUSTOM
Details
The crystals thus precipitated
CUSTOM
Type
CUSTOM
Details
are recrystallized three times from ethanol-water (6:4)

Outcomes

Product
Name
Type
product
Smiles
O.C(=O)(O)C(O)C(O)C(=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
US04397853

Procedure details

A 46.5 g-quantity of the above compound (free base) is dissolved in 200 ml of ethanol, and a solution of 15 g of L-tartaric acid in 200 ml of water is added to the ethanol solution. The resulting mixture is allowed to stand at room temperature. The crystals thus precipitated are recrystallized three times from ethanol-water (6:4) to give tartrate monohydrate as colorless prisms. The tartrate monohydrate is treated with an aqueous solution of sodium bicarbonate to give (-)-1-[5-(4-fluorophenyl)-4,5-dihydroisoxazol-3-ylmethyl]-4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine. Melting point: 143°-145° C. [α]D25 : -108.8 (chloroform).
Quantity
15 g
Type
reactant
Reaction Step One
Name
ethanol
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
200 mL
Type
solvent
Reaction Step One
Quantity
200 mL
Type
solvent
Reaction Step Two

Identifiers

REACTION_CXSMILES
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].FC1C=CC(C2(O)ONC(CN3CCC(N4C5C=CC(Cl)=CC=5NC4=O)CC3)=C2O)=CC=1>C(O)C.O>[OH2:3].[C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7] |f:4.5|

Inputs

Step One
Name
Quantity
15 g
Type
reactant
Smiles
C([C@H](O)[C@@H](O)C(=O)O)(=O)O
Name
ethanol
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC1=CC=C(C=C1)C1(C(=C(NO1)CN1CCC(CC1)N1C(NC2=C1C=CC(=C2)Cl)=O)O)O
Name
Quantity
200 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
200 mL
Type
solvent
Smiles
C(C)O

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
to stand at room temperature
CUSTOM
Type
CUSTOM
Details
The crystals thus precipitated
CUSTOM
Type
CUSTOM
Details
are recrystallized three times from ethanol-water (6:4)

Outcomes

Product
Name
Type
product
Smiles
O.C(=O)(O)C(O)C(O)C(=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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