Reaction #49652

ord-8532a13b49be47c9ad77e4a04bda6575

Reaction equation

CSC
Me2S
O=O.O=[O+][O-]
Ozone oxygen
C=C[C@H](OC(C)=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
(3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene
O=O
Oxygen
→
CC(=O)O[C@@H](C=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
title compound
CC(=O)O[C@@H](C=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
(2R, 3S)-N-[(tert-Butyloxy)carbonyl]-3-amino-2-acetoxy-4-phenylbutanal

Reactants

CSC
Me2S
O=O.O=[O+][O-]
Ozone oxygen
C=C[C@H](OC(C)=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
(3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene
O=O
Oxygen

Reagents

None

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherprepared by the method of Hanson et al., J
  2. 2
    Temperatureto warm to 0°-5° C.
  3. 3
    OtherThe solvent was removed at 0° C. under vacuum

Procedure

Ozone/oxygen was bubbled at -70° C. into a solution of (3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpentene (2.55g, 8.0 mmol) [prepared by the method of Hanson et al., J. Ora. Chem., 50, 5399 (1985)] in 100 mL of methylene chloride until a deep blue color persisted. Oxygen was introduced until the blue color completely faded, then 3.0 mL of Me2S was added and the solution was allowed to warm to 0°-5° C. and stand overnight. The solvent was removed at 0° C. under vacuum yielding the title compound as a thick yellow oil which was used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05422349uspto-grants-1995_06