Chlorosuccinimide → HCID 21314424, compound

HRID 261317Notes

Reaction equation

HRID 261317 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:10]([NH:12][CH:13]1[C:30](=[O:31])[N:15]2[CH:16]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[C:17]([CH3:21])([CH3:20])[S:18](=[O:19])[C@H:14]12)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:38]N1C(=O)CCC1=O>>[CH3:20][C:17](=[CH2:21])[CH:16]([N:15]1[C:30](=[O:31])[CH:13]([NH:12][C:10](=[O:11])[CH:9]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:14]1[S:18]([Cl:38])=[O:19])[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 86735570HCID 86735570, compound

Product 1

HCID 21314424HCID 21314424, compound

Procedure

A solution of 2.85 g. (5 mmol) of 2,2,2-trichloroethyl 6-(α-t-butyloxycarbonylaminophenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide in 175 ml. of toluene was dried azeotropically by distillation of about 50 ml. of toluene from the mixture. To the dried solution was added 0.685 g. (5.5 mmol.) of N-chlorosuccinimide. The resulting mixture was refluxed for 70 minutes. The mixture was allowed to cool to room temperature and then was filtered and evaporated in vacuo to dryness to provide the title product (contaminated with succinimide).

Workup

  1. dry with materialof toluene was dried azeotropically by distillation of about 50 ml
  2. additionTo the dried solution was added 0.685 g
  3. temperatureThe resulting mixture was refluxed for 70 minutes
  4. filtrationwas filtered
  5. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-388cc739396f4d91b63a769c04e2d210
Source dataset
uspto-grants-1979_08
Patent number
US04165315

Reaction notes

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