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

HRID 876369Notes

Reaction equation

HRID 876369 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>CCO.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.[F:15][CH:14]([F:16])[CH2:8][CH2:9][C:10]([O-:12])=[O:11]

Participants

4

Reactant 1

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

Product 2

HCID 211221424,4-DifluorobutanoateYield 43.4%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) by preparative chiral HPLC on Reprosil Chiral NR column with eluent 5% EtOH/n-heptane to give (S)-methyl 3-(5-bromo-2-fluorophenyl)-3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate (1.55 g, 3.6 mmol, 40.8% yield) as a colourless oil and (R)-methyl 3-(5-bromo-2-fluorophenyl)-3-(S)-1,1-dimethylethylsulfinamido)-4,4-difluorobutanoate (1.65 g, 3.83 mmol, 43.4% yield) as a colorless oil.

Sources & evidence

ORD record
ord-9f263817175a47d48d04265692a39074
Source dataset
uspto-grants-2015_03
Patent number
US08987255B2

Reaction notes

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