Acetic acid, 2-bromo-2-fluoro-, ethyl ester → (2R,3R)-3-(5-bromo-2-fluoro-phenyl)-2,4,4-trifluoro-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester

HRID 405712Notes

Reaction equation

HRID 405712 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6](/[C:8](=[N:12]\[S@@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])/[CH:9]([F:11])[F:10])[CH:7]=1.Br[CH:21]([F:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH2:25]([O:24][C:22](=[O:23])[C@H:21]([F:27])[C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:19])([NH:12][S@@:13]([C:15]([CH3:16])([CH3:18])[CH3:17])=[O:14])[CH:9]([F:11])[F:10])[CH3:26].[CH2:25]([O:24][C:22](=[O:23])[C@@H:21]([F:27])[C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:19])([NH:12][S@@:13]([C:15]([CH3:16])([CH3:18])[CH3:17])=[O:14])[CH:9]([F:11])[F:10])[CH3:26]

Participants

4

Reactant 2

HCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 88878981(NE,R)-N-[1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene]-2-methylpropane-2-sulfinamide

Product 2

HCID 88994767(2R,3R)-3-(5-bromo-2-fluoro-phenyl)-2,4,4-trifluoro-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl esterHCID 88994922(2S,3R)-3-(5-bromo-2-fluoro-phenyl)-2,4,4-trifluoro-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester

Procedure

Starting from (R)-2-methyl-propane-2-sulfinic acid [1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-eth-(E)-ylidene]-amide (intermediate A2.3) and ethyl 2-bromo-2-fluoroacetate, a mixture (1 major component) of the 2 diastereoisomers (2R,3R)-3-(5-bromo-2-fluoro-phenyl)-2,4,4-trifluoro-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester and (2S,3R)-3-(5-bromo-2-fluoro-phenyl)-2,4,4-trifluoro-3-((R)-2-methyl-propane-2-sulfinylamino)-butyric acid ethyl ester was obtained as a light yellow viscous oil after chromatography on silica gel (Telos Flash Silica) using a gradient of heptane/ethyl acetate=100:0 to 60:30 as the eluent. MS (ISP): m/z=462.2 [M+H]+and 464.2 [M+2+H]+.

Sources & evidence

ORD record
ord-8cd2b4edf31241b9b4e428109e6350c5
Source dataset
uspto-grants-2014_06
Patent number
US08754075B2

Reaction notes

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