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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
US07132560B2

Procedure details

4′-Cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.20 g, 30.6 mmol) and ethyl acetate (20 ml) were successively charged in a 200 ml four-neck flask, and the mixture was stirred under ice-cooling (2° C.–7° C.). A solution of mono-perphthalic acid in ethyl acetate (166.58 g, net 22.31 g, 122.5 mmol) was dropwise added at not higher than 10° C., and the mixture was stirred for 1 hr. A 20% KOH solution (117.5 g) was dropwise added thereto and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate (30 ml). The combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g) dissolved in deionized water (30 ml), dried over magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (66 ml) was added to the residue and the mixture was heated to 60° C. n-Heptane (40 ml) was added dropwise at a temperature of 60° C.–65° C. over 40 min. After the completion of the dropwise addition, the mixture was allowed to cool to room temperature (about 20° C.–25° C.) and filtrated to give 4′-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.24 g, yield 91.2%). Purity 99.97%.
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
166.58 g
Type
solvent
Reaction Step Two
Name
Quantity
117.5 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C1C=C(C(O)=[O:35])C(C(OO)=O)=CC=1.[OH-:41].[K+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)(=[O:35])=[O:41])=[CH:5][C:4]=1[C:24]([F:27])([F:25])[F:26])#[N:2] |f:2.3|

Inputs

Step One
Name
Quantity
12.2 g
Type
reactant
Smiles
C(#N)C1=C(C=C(NC(C(CSC2=CC=C(C=C2)F)(C)O)=O)C=C1)C(F)(F)F
Name
Quantity
20 mL
Type
solvent
Smiles
C(C)(=O)OCC
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1=CC=C(C(=C1)C(=O)O)C(=O)OO
Name
Quantity
166.58 g
Type
solvent
Smiles
C(C)(=O)OCC
Step Three
Name
Quantity
117.5 g
Type
reactant
Smiles
[OH-].[K+]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
60 °C
Stirring
Type
CUSTOM
Details
the mixture was stirred under ice-
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooling (2° C.–7° C.)
STIRRING
Type
STIRRING
Details
the mixture was stirred for 1 hr
Duration
1 h
CUSTOM
Type
CUSTOM
Details
the mixture was partitioned
EXTRACTION
Type
EXTRACTION
Details
The aqueous layer was extracted with ethyl acetate (30 ml)
WASH
Type
WASH
Details
The combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g)
DISSOLUTION
Type
DISSOLUTION
Details
dissolved in deionized water (30 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CONCENTRATION
Type
CONCENTRATION
Details
concentrated under reduced pressure
ADDITION
Type
ADDITION
Details
Ethyl acetate (66 ml) was added to the residue
ADDITION
Type
ADDITION
Details
was added dropwise at a temperature of 60° C.–65° C. over 40 min
Duration
40 min
ADDITION
Type
ADDITION
Details
After the completion of the dropwise addition
TEMPERATURE
Type
TEMPERATURE
Details
to cool to room temperature (about 20° C.–25° C.)
FILTRATION
Type
FILTRATION
Details
filtrated

Outcomes

Product
Name
Type
product
Smiles
C(#N)C1=C(C=C(NC(C(CS(=O)(=O)C2=CC=C(C=C2)F)(C)O)=O)C=C1)C(F)(F)F
Measurements
Type Value Analysis
AMOUNT: MASS 12.24 g
YIELD: PERCENTYIELD 91.2%

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
US07132560B2

Procedure details

4′-Cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.20 g, 30.6 mmol) and ethyl acetate (20 ml) were successively charged in a 200 ml four-neck flask, and the mixture was stirred under ice-cooling (2° C.–7° C.). A solution of mono-perphthalic acid in ethyl acetate (166.58 g, net 22.31 g, 122.5 mmol) was dropwise added at not higher than 10° C., and the mixture was stirred for 1 hr. A 20% KOH solution (117.5 g) was dropwise added thereto and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate (30 ml). The combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g) dissolved in deionized water (30 ml), dried over magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (66 ml) was added to the residue and the mixture was heated to 60° C. n-Heptane (40 ml) was added dropwise at a temperature of 60° C.–65° C. over 40 min. After the completion of the dropwise addition, the mixture was allowed to cool to room temperature (about 20° C.–25° C.) and filtrated to give 4′-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.24 g, yield 91.2%). Purity 99.97%.
Quantity
20 mL
Type
solvent
Reaction Step One
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
166.58 g
Type
solvent
Reaction Step Two
Name
Quantity
117.5 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C1C=C(C(O)=[O:35])C(C(OO)=O)=CC=1.[OH-:41].[K+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)(=[O:35])=[O:41])=[CH:5][C:4]=1[C:24]([F:27])([F:25])[F:26])#[N:2] |f:2.3|

Inputs

Step One
Name
Quantity
12.2 g
Type
reactant
Smiles
C(#N)C1=C(C=C(NC(C(CSC2=CC=C(C=C2)F)(C)O)=O)C=C1)C(F)(F)F
Name
Quantity
20 mL
Type
solvent
Smiles
C(C)(=O)OCC
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
C1=CC=C(C(=C1)C(=O)O)C(=O)OO
Name
Quantity
166.58 g
Type
solvent
Smiles
C(C)(=O)OCC
Step Three
Name
Quantity
117.5 g
Type
reactant
Smiles
[OH-].[K+]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
60 °C
Stirring
Type
CUSTOM
Details
the mixture was stirred under ice-
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
cooling (2° C.–7° C.)
STIRRING
Type
STIRRING
Details
the mixture was stirred for 1 hr
Duration
1 h
CUSTOM
Type
CUSTOM
Details
the mixture was partitioned
EXTRACTION
Type
EXTRACTION
Details
The aqueous layer was extracted with ethyl acetate (30 ml)
WASH
Type
WASH
Details
The combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g)
DISSOLUTION
Type
DISSOLUTION
Details
dissolved in deionized water (30 ml)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over magnesium sulfate
CONCENTRATION
Type
CONCENTRATION
Details
concentrated under reduced pressure
ADDITION
Type
ADDITION
Details
Ethyl acetate (66 ml) was added to the residue
ADDITION
Type
ADDITION
Details
was added dropwise at a temperature of 60° C.–65° C. over 40 min
Duration
40 min
ADDITION
Type
ADDITION
Details
After the completion of the dropwise addition
TEMPERATURE
Type
TEMPERATURE
Details
to cool to room temperature (about 20° C.–25° C.)
FILTRATION
Type
FILTRATION
Details
filtrated

Outcomes

Product
Name
Type
product
Smiles
C(#N)C1=C(C=C(NC(C(CS(=O)(=O)C2=CC=C(C=C2)F)(C)O)=O)C=C1)C(F)(F)F
Measurements
Type Value Analysis
AMOUNT: MASS 12.24 g
YIELD: PERCENTYIELD 91.2%

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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