tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamate → HCID 86591235, compound

HRID 132809Notes

Reaction equation

HRID 132809 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[F:5][C:6]1[CH:7]=[C:8]([CH2:13][C@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@@H:15]2[CH2:17][O:16]2)[CH:9]=[C:10]([F:12])[CH:11]=1>O1CCCC1>[F:5][C:6]1[CH:7]=[C:8]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:13][C@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C@@H:15]([OH:16])[CH2:17][CH:1]=[CH2:2]

Participants

4

Reactant 2

HCID 11415322tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamateHCID 178418507HCID 178418507, compound

Product 1

HCID 86591235HCID 86591235, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Vinylmagnesium bromide was added to copper (I) bromide-dimethyl sulfide complex in tetrahydrofuran at low temperature. Tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2R)-oxiran-2-yl]ethylcarbamate (31) in tetrahydrofuran was added. At room temperature, the reaction was quenched with saturated ammonium chloride, extracted, and dried over sodium sulfate. A white solid (32) was obtained upon concentration.

Workup

  1. customAt room temperature, the reaction was quenched with saturated ammonium chloride
  2. extractionextracted
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-8870f93760e241d8b15bcccffb743adc
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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