N-Iodosuccinimide → HCID 53841299, compound

HRID 1164195Notes

Reaction equation

HRID 1164195 reaction equation
[CH3:1][C:2](=[CH2:36])[CH:3]([N:17]1[CH:20](S(O)=O)[CH:19]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:18]1=[O:35])[C:4]([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].[I:37]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][C:2](=[CH2:36])[CH:3]([N:17]1[CH:20]([I:37])[CH:19]([NH:24][C:25](=[O:34])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:18]1=[O:35])[C:4]([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]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 13071358HCID 13071358, compound

Product 1

HCID 53841299HCID 53841299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of p-nitrobenzyl 3-methyl-2-(2-oxo-4-sulfino-3-phenoxyacetamido-1-azetidinyl)-3-butenoate in methylene chloride was cooled to 0° C. and one molar equivalent of N-iodosuccinimide was added with stirring. After 5 minutes the reaction mixture was washed with brine, dried and evaporated. The product obtained as a solid residue was shown by its nmr spectrum to contain about a 2:1 ratio of cis-isomer to trans-isomer contaminated with a trace of oxazolineazetidinone.

Workup

  1. washAfter 5 minutes the reaction mixture was washed with brine
  2. customdried
  3. customevaporated
  4. customThe product obtained as a solid residue

Sources & evidence

ORD record
ord-e8b967ac409f4bafad2298e4007547c4
Source dataset
uspto-grants-1983_01
Patent number
US04368156

Reaction notes

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