Oxygen → HCID 54383686, compound

HRID 1603655Notes

Reaction equation

HRID 1603655 reaction equation
O=O.[CH2:3]([S:10][C@H:11]1[N:14](C(=C(C)C)C(OCC2C=CC(OC)=CC=2)=O)[C:13](=[O:31])[C@@H:12]1[Br:32])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[O-].[Na+].CSC>ClCCl.CO>[CH2:3]([S:10][C@H:11]1[NH:14][C:13](=[O:31])[C@@H:12]1[Br:32])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 10942334Sodium MethoxideHCID 86754829HCID 86754829, compound

Product 1

HCID 54383686HCID 54383686, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozonised oxygen was bubbled through a solution of p-methoxybenzyl 2-[(3S, 4R)-4-benzylthio-3-bromo-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (2 g, 4 mmol) in dichloromethane (40 ml) at -78° C. and the reaction monitored by infra-red spectroscopy. When the band at 1780 cm-1 had disappeared, methanol (4 ml) together with a trace of sodium methoxide and dimethyl sulfide (1 ml) was added and stirring continued at room temperature for 16 h. The reaction was evaporated and the residue purified by flash chromatography using 1:1 ether:pentane as the eluting solvent. Evaporation of the appropriate fractions gave the product as a colourless oil (0.7 g, 64%). 1H NMR δ (CDCl3) 3.87 (2H, s, SCH2), 4.52 (1H, m, H4), 4.69 (1H, d, H3) 5.85 (1H, bs, NH), 7.18-7.39 (5H, m, Ph--H).

Workup

  1. customThe reaction was evaporated
  2. customthe residue purified by flash chromatography
  3. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-e853c40451bf4f3189242e114ed929e7
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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