Clopidogrel Camphorsulfonate
货号 B8563496
分子量: 554.1 g/mol
InChI 键: XEENARPWPCQXST-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
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
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
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. |
