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

HRID 413805Notes

Reaction equation

HRID 413805 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]([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:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.ClCCl>[CH2:3]([O:10][C:11]([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:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

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 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of potassium hydroxide (6.52 g. 0.116 mol. 1.2 equiv.) in 970 mL of absolute ethanol was treated with N-benzyloxycarbonyl-3(S)-amino-1-chloro-4-phenyl-2(s)-butanol (32.3 g, 0.097 mol). This solution was stirred at room temperature for 15 minutes and then concentrated in vacuo to give a white solid. The solid was dissolved in dichloromethane and washed with water, dried over anhyd MgSO4, filtered and concentrated in vacuo to give a white solid. The solid was crystallized from hexanes and ethyl acetate to give 22.3 g, 77% of 3(S)-[N-(benzyloxycarbonyl) amino]-1,2(S)-epoxy-4-phenylbutane, mp 102-103° C., FAB MS: MH+=298.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a white solid
  3. washwashed with water
  4. dry with materialdried over anhyd MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a white solid
  8. customThe solid was crystallized from hexanes and ethyl acetate

Sources & evidence

ORD record
ord-b4bfcd4bfd4d46e4940fd2e7d5632538
Source dataset
uspto-grants-2003_05
Patent number
US06569882B2

Reaction notes

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