Potassium Hydroxide → (2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

HRID 54067

Reaction equation

HRID 54067 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:13]([OH:16])[CH2:14]Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:13]1[O:16][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10860587Benzyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

Product 1

HCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutaneYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.4 g of 3(S)-(benzyloxyformamido)-1-chloro-4-phenyl-2(S)-butanol in 300 ml of ethanol containing 2.24 g of potassium hydroxide was left to stand for 15 minutes. The solvent was removed by evaporation and the residue was partitioned between water and dichloromethane. Working-up gave 10.1 g of crude 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane as an off-white solid which was used without further purification.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between water and dichloromethane

Sources & evidence

ORD record
ord-6ad909a6484b4f0ba9bd467981f97cca
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Linked notes

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