(S)-Bicalutamide-d4
Número de catálogo B1140949
Peso molecular: 434.4
Clave InChI:
Atención: Solo para uso de investigación. No para uso humano o veterinario.
Patent
US07199257B1
Procedure details
To a solution of 2 g (2.51 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 10 ml of acetonitrile, 20 ml of methanol and 0.6 ml of water 0.38 g (2.75 mmol) of potassium carbonate was added. The mixture was cooled to 5° C. and 10 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was stirred at 25° C. overnight, then diluted with 100 ml of water and extracted twice with 100 ml of dichloromethane. The organic layer was washed with 50 ml of brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C. The yield was 1.53 g (70.83%).
Quantity
2 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C(=O)([O-])[O-:29].[K+].[K+].OO.[OH2:36]>C(#N)C.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:29])=[O:36])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2] |f:1.2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
|
reactant
|
|
Smiles
|
C(#N)C1=C(C=C(C=C1)NC(C(CSC1=CC=C(C=C1)F)(C)O)=O)C(F)(F)F
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[K+].[K+]
|
|
Name
|
|
|
Quantity
|
0.6 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)#N
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Two
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
OO
|
Step Three
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
5 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred at 25° C. overnight
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted twice with 100 ml of dichloromethane
|
WASH
|
Type
|
WASH
|
|
Details
|
The organic layer was washed with 50 ml of brine
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried over sodium sulfate
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
concentrated under diminished pressure
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(#N)C1=C(C=C(C=C1)NC(C(CS(=O)(=O)C1=CC=C(C=C1)F)(C)O)=O)C(F)(F)F
|
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
US07199257B1
Procedure details
To a solution of 2 g (2.51 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 10 ml of acetonitrile, 20 ml of methanol and 0.6 ml of water 0.38 g (2.75 mmol) of potassium carbonate was added. The mixture was cooled to 5° C. and 10 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was stirred at 25° C. overnight, then diluted with 100 ml of water and extracted twice with 100 ml of dichloromethane. The organic layer was washed with 50 ml of brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C. The yield was 1.53 g (70.83%).
Quantity
2 g
Type
reactant
Reaction Step One
Identifiers
|
REACTION_CXSMILES
|
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C(=O)([O-])[O-:29].[K+].[K+].OO.[OH2:36]>C(#N)C.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:29])=[O:36])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2] |f:1.2.3|
|
Inputs
Step One
|
Name
|
|
|
Quantity
|
2 g
|
|
Type
|
reactant
|
|
Smiles
|
C(#N)C1=C(C=C(C=C1)NC(C(CSC1=CC=C(C=C1)F)(C)O)=O)C(F)(F)F
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
|
Smiles
|
C([O-])([O-])=O.[K+].[K+]
|
|
Name
|
|
|
Quantity
|
0.6 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
solvent
|
|
Smiles
|
C(C)#N
|
|
Name
|
|
|
Quantity
|
20 mL
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Two
|
Name
|
|
|
Quantity
|
10 mL
|
|
Type
|
reactant
|
|
Smiles
|
OO
|
Step Three
|
Name
|
|
|
Quantity
|
100 mL
|
|
Type
|
reactant
|
|
Smiles
|
O
|
Conditions
Temperature
|
Control Type
|
UNSPECIFIED
|
|
Setpoint
|
5 °C
|
Stirring
|
Type
|
CUSTOM
|
|
Details
|
The mixture was stirred at 25° C. overnight
|
|
Rate
|
UNSPECIFIED
|
|
RPM
|
0
|
Other
|
Conditions are dynamic
|
1
|
|
Details
|
See reaction.notes.procedure_details.
|
Workups
EXTRACTION
|
Type
|
EXTRACTION
|
|
Details
|
extracted twice with 100 ml of dichloromethane
|
WASH
|
Type
|
WASH
|
|
Details
|
The organic layer was washed with 50 ml of brine
|
DRY_WITH_MATERIAL
|
Type
|
DRY_WITH_MATERIAL
|
|
Details
|
dried over sodium sulfate
|
CONCENTRATION
|
Type
|
CONCENTRATION
|
|
Details
|
concentrated under diminished pressure
|
CUSTOM
|
Type
|
CUSTOM
|
|
Details
|
The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which
|
Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
|
Name
|
|
|
Type
|
|
|
Smiles
|
C(#N)C1=C(C=C(C=C1)NC(C(CS(=O)(=O)C1=CC=C(C=C1)F)(C)O)=O)C(F)(F)F
|
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. |
