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

HRID 428794Notes

Reaction equation

HRID 428794 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-2ad59bef2fd54e17b3e722a66a57e6a6
Source dataset
uspto-grants-2001_11
Patent number
US06313345B1

Reaction notes

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