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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
US07186854B2

Procedure details

0.500 g of the epoxyamide (5A) was dissolved in a mixture of 40 ml of chloroform and 40 ml of water and 371 mg of sodium p-fluorobenzenesulfinate was added. Subsequently, 298 mg of tetrabutylammonium bromide was added. The reaction mixture was heated till reflux, while stirring vigorously. The reaction was monitored with HPLC. After 96 hours of reflux, the reaction mixture was cooled to room temperature. 20 ml of chloroform was added and the organic layer was washed with 3×50 ml of water, dried (Na2SO4) and evaporated to dryness. Yield: 860 mg. Purification of the crude product by column chromatography (Merck silica gel 60; eluent: heptane/ethyl acetate=1/1) afforded bicalutamide as white solid. Isolated yield: 380 mg (48%). 1H-NMR: confirmed the structure.
Quantity
0.5 g
Type
reactant
Reaction Step One
Name
sodium p-fluorobenzenesulfinate
Quantity
371 mg
Type
reactant
Reaction Step One
Quantity
40 mL
Type
solvent
Reaction Step One
Name
Quantity
40 mL
Type
solvent
Reaction Step One
Quantity
298 mg
Type
catalyst
Reaction Step Two
Quantity
20 mL
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2([CH3:15])[CH2:14][O:13]2)=[O:11])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.[Na+]>C(Cl)(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][C:12]([OH:13])([C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:5]=1)=[O:11])[CH2:14][S:27]([C:24]1[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=1)(=[O:29])=[O:28] |f:1.2,5.6|

Inputs

Step One
Name
Quantity
0.5 g
Type
reactant
Smiles
C(#N)C1=C(C=C(C=C1)NC(=O)C1(OC1)C)C(F)(F)F
Name
sodium p-fluorobenzenesulfinate
Quantity
371 mg
Type
reactant
Smiles
FC1=CC=C(C=C1)S(=O)[O-].[Na+]
Name
Quantity
40 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl
Name
Quantity
40 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
298 mg
Type
catalyst
Smiles
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC
Step Three
Name
Quantity
20 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
while stirring vigorously
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
till reflux
TEMPERATURE
Type
TEMPERATURE
Details
After 96 hours of reflux
Duration
96 h
WASH
Type
WASH
Details
the organic layer was washed with 3×50 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried (Na2SO4)
CUSTOM
Type
CUSTOM
Details
evaporated to dryness
CUSTOM
Type
CUSTOM
Details
Purification of the crude product by column chromatography (Merck silica gel 60; eluent: heptane/ethyl acetate=1/1)

Outcomes

Product
Name
Type
product
Smiles
CC(CS(=O)(=O)C=1C=CC(=CC1)F)(C(=O)NC=2C=CC(=C(C2)C(F)(F)F)C#N)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
US07186854B2

Procedure details

0.500 g of the epoxyamide (5A) was dissolved in a mixture of 40 ml of chloroform and 40 ml of water and 371 mg of sodium p-fluorobenzenesulfinate was added. Subsequently, 298 mg of tetrabutylammonium bromide was added. The reaction mixture was heated till reflux, while stirring vigorously. The reaction was monitored with HPLC. After 96 hours of reflux, the reaction mixture was cooled to room temperature. 20 ml of chloroform was added and the organic layer was washed with 3×50 ml of water, dried (Na2SO4) and evaporated to dryness. Yield: 860 mg. Purification of the crude product by column chromatography (Merck silica gel 60; eluent: heptane/ethyl acetate=1/1) afforded bicalutamide as white solid. Isolated yield: 380 mg (48%). 1H-NMR: confirmed the structure.
Quantity
0.5 g
Type
reactant
Reaction Step One
Name
sodium p-fluorobenzenesulfinate
Quantity
371 mg
Type
reactant
Reaction Step One
Quantity
40 mL
Type
solvent
Reaction Step One
Name
Quantity
40 mL
Type
solvent
Reaction Step One
Quantity
298 mg
Type
catalyst
Reaction Step Two
Quantity
20 mL
Type
solvent
Reaction Step Three

Identifiers

REACTION_CXSMILES
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2([CH3:15])[CH2:14][O:13]2)=[O:11])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17])#[N:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.[Na+]>C(Cl)(Cl)Cl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:15][C:12]([OH:13])([C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:5]=1)=[O:11])[CH2:14][S:27]([C:24]1[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=1)(=[O:29])=[O:28] |f:1.2,5.6|

Inputs

Step One
Name
Quantity
0.5 g
Type
reactant
Smiles
C(#N)C1=C(C=C(C=C1)NC(=O)C1(OC1)C)C(F)(F)F
Name
sodium p-fluorobenzenesulfinate
Quantity
371 mg
Type
reactant
Smiles
FC1=CC=C(C=C1)S(=O)[O-].[Na+]
Name
Quantity
40 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl
Name
Quantity
40 mL
Type
solvent
Smiles
O
Step Two
Name
Quantity
298 mg
Type
catalyst
Smiles
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC
Step Three
Name
Quantity
20 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
while stirring vigorously
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
till reflux
TEMPERATURE
Type
TEMPERATURE
Details
After 96 hours of reflux
Duration
96 h
WASH
Type
WASH
Details
the organic layer was washed with 3×50 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried (Na2SO4)
CUSTOM
Type
CUSTOM
Details
evaporated to dryness
CUSTOM
Type
CUSTOM
Details
Purification of the crude product by column chromatography (Merck silica gel 60; eluent: heptane/ethyl acetate=1/1)

Outcomes

Product
Name
Type
product
Smiles
CC(CS(=O)(=O)C=1C=CC(=CC1)F)(C(=O)NC=2C=CC(=C(C2)C(F)(F)F)C#N)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.
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