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

HRID 1738998Notes

Reaction equation

HRID 1738998 reaction equation
[OH-].[K+].[C:3]([NH:13][C@@H:14]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:15]([OH:18])[CH2:16]Cl)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]>C(O)C>[CH2:6]([O:5][C:3]([NH:13][C@@H:14]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:15]1[O:18][CH2:16]1)=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=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-phenylbutane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.2 equiv. of potassium hydroxide in 968 mL of absolute ethanol at room temperature, is added 0.097 mol of N-CBZ-3(S)-amino-1-chloro-4-phenyl-2(S)-butanol. After stirring for fifteen minutes, the solvent is removed under reduced pressure and the solids are dissolved in methylene chloride. After washing with water, drying over magnesium sulfate, filtering and stripping, one obtains a white solid. Recrystallization from hot ethyl acetate and hexane will afford N-benzyloxycarbonyl-3(S)-amino-1,2(S)-epoxy-4-phenylbutane.

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionthe solids are dissolved in methylene chloride
  3. washAfter washing with water
  4. dry with materialdrying over magnesium sulfate
  5. filtrationfiltering
  6. customone obtains a white solid
  7. customRecrystallization from hot ethyl acetate and hexane

Sources & evidence

ORD record
ord-b539aa34d5ee4979bcbe25624dc495ab
Source dataset
uspto-grants-1999_10
Patent number
US05965588

Reaction notes

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