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molecular formula C26H32ClNO6S2 B8563496 Clopidogrel Camphorsulfonate

Clopidogrel Camphorsulfonate

Cat. No. B8563496
M. Wt: 554.1 g/mol
InChI Key: XEENARPWPCQXST-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US06215005B1

Procedure details

32 g (0.0994 mol) of (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is dissolved in 150 ml of acetone and to the solution 9.95 g (0.0397 mol) of laevorotatory 10-camphorsulfonic acid monohydrate is added. The homogenous reaction mixture is allowed to stay at room temperature. After 48 hours a few crystals appear. The mixture is concentrated by evaporation to 50 ml and allowed to stay at room temperature for 24 hours. The resulting crystals are filtered off, washed with acetone and dried. The crystals thus obtained are dissolved again in a very small amount (50 ml) of hot acetone and after cooling the crystals are filtered off, washed with acetone and dried. Thus the title compound is obtained. Yield: 88%. Mp.: 165° C. [α]20D=+24° (c=1.68 g/100 ml; methanol).
Name
(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester
Quantity
32 g
Type
reactant
Reaction Step One
Quantity
9.95 g
Type
reactant
Reaction Step One
Quantity
150 mL
Type
solvent
Reaction Step One
Quantity
50 mL
Type
solvent
Reaction Step Two
Yield
88%

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1.O.[C:23]12([CH2:33][S:34]([OH:37])(=[O:36])=[O:35])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25]>CC(C)=O>[C:23]12([CH2:33][S:34]([OH:37])(=[O:35])=[O:36])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25].[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1 |f:1.2,4.5|

Inputs

Step One
Name
(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester
Quantity
32 g
Type
reactant
Smiles
COC(C(N1CC2=C(CC1)SC=C2)C2=C(C=CC=C2)Cl)=O
Name
Quantity
9.95 g
Type
reactant
Smiles
O.C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O
Name
Quantity
150 mL
Type
solvent
Smiles
CC(=O)C
Step Two
Name
Quantity
50 mL
Type
solvent
Smiles
CC(=O)C

Conditions

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

Workups

ADDITION
Type
ADDITION
Details
is added
CUSTOM
Type
CUSTOM
Details
to stay at room temperature
CONCENTRATION
Type
CONCENTRATION
Details
The mixture is concentrated by evaporation to 50 ml
WAIT
Type
WAIT
Details
to stay at room temperature for 24 hours
Duration
24 h
FILTRATION
Type
FILTRATION
Details
The resulting crystals are filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried
CUSTOM
Type
CUSTOM
Details
The crystals thus obtained
TEMPERATURE
Type
TEMPERATURE
Details
after cooling the crystals
FILTRATION
Type
FILTRATION
Details
are filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
48 h
Name
Type
product
Smiles
C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O.COC(C(N2CC1=C(CC2)SC=C1)C1=C(C=CC=C1)Cl)=O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 88%

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
US06215005B1

Procedure details

32 g (0.0994 mol) of (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is dissolved in 150 ml of acetone and to the solution 9.95 g (0.0397 mol) of laevorotatory 10-camphorsulfonic acid monohydrate is added. The homogenous reaction mixture is allowed to stay at room temperature. After 48 hours a few crystals appear. The mixture is concentrated by evaporation to 50 ml and allowed to stay at room temperature for 24 hours. The resulting crystals are filtered off, washed with acetone and dried. The crystals thus obtained are dissolved again in a very small amount (50 ml) of hot acetone and after cooling the crystals are filtered off, washed with acetone and dried. Thus the title compound is obtained. Yield: 88%. Mp.: 165° C. [α]20D=+24° (c=1.68 g/100 ml; methanol).
Name
(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester
Quantity
32 g
Type
reactant
Reaction Step One
Quantity
9.95 g
Type
reactant
Reaction Step One
Quantity
150 mL
Type
solvent
Reaction Step One
Quantity
50 mL
Type
solvent
Reaction Step Two
Yield
88%

Identifiers

REACTION_CXSMILES
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1.O.[C:23]12([CH2:33][S:34]([OH:37])(=[O:36])=[O:35])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25]>CC(C)=O>[C:23]12([CH2:33][S:34]([OH:37])(=[O:35])=[O:36])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25].[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1 |f:1.2,4.5|

Inputs

Step One
Name
(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester
Quantity
32 g
Type
reactant
Smiles
COC(C(N1CC2=C(CC1)SC=C2)C2=C(C=CC=C2)Cl)=O
Name
Quantity
9.95 g
Type
reactant
Smiles
O.C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O
Name
Quantity
150 mL
Type
solvent
Smiles
CC(=O)C
Step Two
Name
Quantity
50 mL
Type
solvent
Smiles
CC(=O)C

Conditions

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

Workups

ADDITION
Type
ADDITION
Details
is added
CUSTOM
Type
CUSTOM
Details
to stay at room temperature
CONCENTRATION
Type
CONCENTRATION
Details
The mixture is concentrated by evaporation to 50 ml
WAIT
Type
WAIT
Details
to stay at room temperature for 24 hours
Duration
24 h
FILTRATION
Type
FILTRATION
Details
The resulting crystals are filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried
CUSTOM
Type
CUSTOM
Details
The crystals thus obtained
TEMPERATURE
Type
TEMPERATURE
Details
after cooling the crystals
FILTRATION
Type
FILTRATION
Details
are filtered off
WASH
Type
WASH
Details
washed with acetone
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Details
Reaction Time
48 h
Name
Type
product
Smiles
C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O.COC(C(N2CC1=C(CC2)SC=C1)C1=C(C=CC=C1)Cl)=O
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 88%

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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