Sodium Hydroxide → tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((R)-oxiran-2-yl)ethyl)carbamate

HRID 132808Notes

Reaction equation

HRID 132808 reaction equation
C(O[CH2:10][C@@H:11]([O:30]S(C)(=O)=O)[C@@H:12]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=1)(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.O.O>[F:20][C:18]1[CH:19]=[C:14]([CH2:13][C@H:12]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C@@H:11]2[CH2:10][O:30]2)[CH:15]=[C:16]([F:21])[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86591234HCID 86591234, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Mesylate 30 was dissolved in methanol/water at 0° and a solution of sodium hydroxide in water was added. After all of the starting material was consumed, the reaction was extracted and the residue purified using silica gel chromatography to obtain epoxide 31 as a white solid, m.p.=99°.

Workup

  1. customAfter all of the starting material was consumed
  2. extractionthe reaction was extracted
  3. customthe residue purified

Sources & evidence

ORD record
ord-3d3853ff46f0442b9c10b4a6c04efd6c
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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