methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate → (S)-methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate

HRID 1626085Notes

Reaction equation

HRID 1626085 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C:8]([NH:17][S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([CH:14]([F:16])[F:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=1>C(O)C.CCCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C@:8]([NH:17][S@:18]([C:20]([CH3:22])([CH3:21])[CH3:23])=[O:19])([CH:14]([F:16])[F:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=1

Participants

3

Reactant 1

HCID 71009051methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate

Product 1

HCID 71008874(S)-methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoateYield 40.8%

Reagents, catalysts & solvents 1

HCID 22502148Ethanol heptaneSolvent

Procedure

Chiral separation of methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate (3.8 g, 8.83 mmol) (intermediate A3.14) by preparative chiral HPLC on Reprosil Chiral NR column with a mixture of 5% ethanol/n-heptane as the eluent yielded the (S)-methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate (1.55 g, 40.8% yield) (intermediate A3.15) as a colorless oil and the (R)-methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate (1.65 g, 43.4% yield)) (intermediate A3.15) as a colorless oil.

Sources & evidence

ORD record
ord-4f59c42f295b42a49e6c21daf85d2cf2
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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