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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:
Attention: For research use only. Not for human or veterinary use.
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Patent
US07186854B2

Procedure details

180 mg of the chiral epoxide of example 17 was dissolved in a mixture of 12 ml chloroform and 12 ml of water. 133 mg of sodium-p-fluorobenzenesulfinate and 107 mg of tetrabutylammonium bromide were added. The reaction mixture was heated till reflux and kept at reflux, while stirring vigorously. The reaction was monitored with HPLC. After 4 days at reflux, the starting epoxide was completely converted. The mixture was cooled to room temperature. 10 ml of chloroform was added. The organic layer was washed with 3×20 ml of water, dried (Na2SO4), filtrated and evaporated to dryness. Residue: 226 mg (brown oil). Purification of the residue by column chromatography (Merck silica gel 60; eluens: heptane/ethyl acetate=1/1) afforded R-enantiomer of bicalutamide as a white/yellow solid material. Purified yield: 122 mg (43%). HPLC: 96.3% purity. HPLC (chiral column): 94.7% e.e. 1H and 13C NMR in agreement with R-bicalutamide
Quantity
180 mg
Type
reactant
Reaction Step One
Quantity
12 mL
Type
solvent
Reaction Step One
Name
Quantity
12 mL
Type
solvent
Reaction Step One
Name
sodium p-fluorobenzenesulfinate
Quantity
133 mg
Type
reactant
Reaction Step Two
Quantity
107 mg
Type
catalyst
Reaction Step Two
[Compound]
Name
epoxide
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
10 mL
Type
solvent
Reaction Step Four

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].[Na].[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O-:30])=[O:29])=[CH:24][CH:23]=1>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:28]([C:25]1[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=1)(=[O:30])=[O:29] |f:1.2,5.6,^1:19|

Inputs

Step One
Name
Quantity
180 mg
Type
reactant
Smiles
C(#N)C1=C(C=C(C=C1)NC(=O)[C@]1(OC1)C)C(F)(F)F
Name
Quantity
12 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl
Name
Quantity
12 mL
Type
solvent
Smiles
O
Step Two
Name
sodium p-fluorobenzenesulfinate
Quantity
133 mg
Type
reactant
Smiles
[Na].FC1=CC=C(C=C1)S(=O)[O-]
Name
Quantity
107 mg
Type
catalyst
Smiles
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC
Step Three
Name
epoxide
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
10 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

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
till reflux
TEMPERATURE
Type
TEMPERATURE
Details
at reflux
TEMPERATURE
Type
TEMPERATURE
Details
After 4 days at reflux
Duration
4 d
WASH
Type
WASH
Details
The organic layer was washed with 3×20 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried (Na2SO4)
FILTRATION
Type
FILTRATION
Details
filtrated
CUSTOM
Type
CUSTOM
Details
evaporated to dryness
CUSTOM
Type
CUSTOM
Details
Purification of the residue by column chromatography (Merck silica gel 60; eluens: 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

180 mg of the chiral epoxide of example 17 was dissolved in a mixture of 12 ml chloroform and 12 ml of water. 133 mg of sodium-p-fluorobenzenesulfinate and 107 mg of tetrabutylammonium bromide were added. The reaction mixture was heated till reflux and kept at reflux, while stirring vigorously. The reaction was monitored with HPLC. After 4 days at reflux, the starting epoxide was completely converted. The mixture was cooled to room temperature. 10 ml of chloroform was added. The organic layer was washed with 3×20 ml of water, dried (Na2SO4), filtrated and evaporated to dryness. Residue: 226 mg (brown oil). Purification of the residue by column chromatography (Merck silica gel 60; eluens: heptane/ethyl acetate=1/1) afforded R-enantiomer of bicalutamide as a white/yellow solid material. Purified yield: 122 mg (43%). HPLC: 96.3% purity. HPLC (chiral column): 94.7% e.e. 1H and 13C NMR in agreement with R-bicalutamide
Quantity
180 mg
Type
reactant
Reaction Step One
Quantity
12 mL
Type
solvent
Reaction Step One
Name
Quantity
12 mL
Type
solvent
Reaction Step One
Name
sodium p-fluorobenzenesulfinate
Quantity
133 mg
Type
reactant
Reaction Step Two
Quantity
107 mg
Type
catalyst
Reaction Step Two
[Compound]
Name
epoxide
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Quantity
10 mL
Type
solvent
Reaction Step Four

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].[Na].[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O-:30])=[O:29])=[CH:24][CH:23]=1>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:28]([C:25]1[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=1)(=[O:30])=[O:29] |f:1.2,5.6,^1:19|

Inputs

Step One
Name
Quantity
180 mg
Type
reactant
Smiles
C(#N)C1=C(C=C(C=C1)NC(=O)[C@]1(OC1)C)C(F)(F)F
Name
Quantity
12 mL
Type
solvent
Smiles
C(Cl)(Cl)Cl
Name
Quantity
12 mL
Type
solvent
Smiles
O
Step Two
Name
sodium p-fluorobenzenesulfinate
Quantity
133 mg
Type
reactant
Smiles
[Na].FC1=CC=C(C=C1)S(=O)[O-]
Name
Quantity
107 mg
Type
catalyst
Smiles
[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC
Step Three
Name
epoxide
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
10 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

TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was heated
TEMPERATURE
Type
TEMPERATURE
Details
till reflux
TEMPERATURE
Type
TEMPERATURE
Details
at reflux
TEMPERATURE
Type
TEMPERATURE
Details
After 4 days at reflux
Duration
4 d
WASH
Type
WASH
Details
The organic layer was washed with 3×20 ml of water
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried (Na2SO4)
FILTRATION
Type
FILTRATION
Details
filtrated
CUSTOM
Type
CUSTOM
Details
evaporated to dryness
CUSTOM
Type
CUSTOM
Details
Purification of the residue by column chromatography (Merck silica gel 60; eluens: 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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