(R)-Amlodipine
货号 B1678800
分子量: 408.9 g/mol
InChI 键: HTIQEAQVCYTUBX-QGZVFWFLSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US06846932B1
Procedure details
To a stirred solution of 100 gm (0.245 moles) of RS amlodipine in 150 ml DMSO was added a solution of 9.2 gm (0.06 moles, 0.25 eq) of L (+) tartaric acid in 100 ml DMSO. The solid starts separating from clear solution within 5-10 mins. This was stirred for 3 hrs and solid was filtered off, washed with acetone and dried to give 58.6 gm (40.5%) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate. mp. 160-162° C., 96.8% d.e. by chiral HPLC.
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CS(C)=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([O-:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([O-:36])=[O:35])[OH:33])[OH:31]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C(O)C(O)C(=O)O)(=O)O
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
CS(=O)C
|
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
solvent
|
|
Smiles
|
CS(=O)C
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
This was stirred for 3 hrs
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solid starts separating from clear solution within 5-10 mins
|
|
Duration
|
7.5 (± 2.5) min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
solid was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with acetone
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
3 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
|
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C([C@H](O)[C@@H](O)C(=O)[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
US06846932B1
Procedure details
To a stirred solution of 100 gm (0.245 moles) of RS amlodipine in 150 ml DMSO was added a solution of 9.2 gm (0.06 moles, 0.25 eq) of L (+) tartaric acid in 100 ml DMSO. The solid starts separating from clear solution within 5-10 mins. This was stirred for 3 hrs and solid was filtered off, washed with acetone and dried to give 58.6 gm (40.5%) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate. mp. 160-162° C., 96.8% d.e. by chiral HPLC.
Identifiers
|
REACTION_CXSMILES
|
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CS(C)=O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[C:29]([O-:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([O-:36])=[O:35])[OH:33])[OH:31]
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C(C1C=2C=CC=CC2Cl)C(=O)OC)C)COCCN
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C(C(O)C(O)C(=O)O)(=O)O
|
|
Name
|
|
|
Quantity
|
150 mL
|
|
Type
|
solvent
|
|
Smiles
|
CS(=O)C
|
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
solvent
|
|
Smiles
|
CS(=O)C
|
Conditions
Stirring
|
Type
|
CUSTOM
|
|
Details
|
This was stirred for 3 hrs
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The solid starts separating from clear solution within 5-10 mins
|
|
Duration
|
7.5 (± 2.5) min
|
FILTRATION
|
Type
|
FILTRATION
|
|
Details
|
solid was filtered off
|
WASH
|
Type
|
WASH
|
|
Details
|
washed with acetone
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
dried
|
Outcomes
Product
Details
Reaction Time |
3 h |
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
|
|
Name
|
|
|
Type
|
product
|
|
Smiles
|
C([C@H](O)[C@@H](O)C(=O)[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. |
