Oxygen → (2R,3S)-N-(tert-Butyloxy)carbonyl-3-amino-2-acetoxy-4-phenylbutanal

HRID 21374Notes

Reaction equation

HRID 21374 reaction equation
O=[O+][O-].[O:4]=O.[C:6]([O:10][C:11]([NH:13][C@@H:14]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:15]([O:18][C:19](=[O:21])[CH3:20])[CH:16]=C)=[O:12])([CH3:9])([CH3:8])[CH3:7].O=O.S(C)C>C(Cl)Cl>[C:6]([O:10][C:11]([NH:13][C@@H:14]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C@@H:15]([O:18][C:19](=[O:21])[CH3:20])[CH:16]=[O:4])=[O:12])([CH3:7])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 10980116(3S,4S)-N-[(tert-Butyloxy)carbonyl]-4-amino-3-acetoxy-5-phenylpenteneHCID 131711318Oxygen ozone

Product 1

HCID 14856784(2R,3S)-N-(tert-Butyloxy)carbonyl-3-amino-2-acetoxy-4-phenylbutanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-8532a13b49be47c9ad77e4a04bda6575
Source dataset
uspto-grants-1995_06
Patent number
US05422349

Reaction notes

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