4-Acetylthio-2-azetidinone → HCID 13132061, compound

HRID 355214Notes

Reaction equation

HRID 355214 reaction equation
O.[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:5])[CH:3]=[O:4].[C:17]([S:20][CH:21]1[NH:24][C:23](=[O:25])[CH2:22]1)(=[O:19])[CH3:18]>C1C=CC=CC=1>[C:17]([S:20][CH:21]1[N:24]([CH:3]([OH:4])[C:2]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:5])[C:23](=[O:25])[CH2:22]1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 131320584-Acetylthio-2-azetidinoneHCID 21934455p-Nitrobenzyl glyoxylate hydrate

Product 1

HCID 13132061HCID 13132061, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Nitrobenzyl glyoxylate hydrate (63.4 g., 0.278 mole) was added to a solution of 4-acetylthio-2-azetidinone (36.2 g., 0.250 mole) in 1200 ml. of benzene. The mixture was refluxed for 17 hours in a Dean-Stark apparatus. The solution was concentrated on a rotary evaporator to give the title product as a yellow oil (102 g., 100%). This oil was found to be identical with the product of Preparation 2A-1.

Workup

  1. temperatureThe mixture was refluxed for 17 hours in a Dean-Stark apparatus
  2. concentrationThe solution was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8d7fe5f6b6044f16b26ec8990b5f0f14
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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