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molecular formula C₁₈H₁₀D₄F₄N₂O₄S B1140949 (S)-Bicalutamide-d4 CAS No. 1217769-79-3

(S)-Bicalutamide-d4

Cat. No. B1140949
M. Wt: 434.4
InChI Key:
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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
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0.6 mL
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
10 mL
Type
reactant
Reaction Step Two

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
0 (± 1) mol
Type
reactant
Reaction Step One
Name
Quantity
0.6 mL
Type
reactant
Reaction Step One
Quantity
10 mL
Type
solvent
Reaction Step One
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
10 mL
Type
reactant
Reaction Step Two

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.
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