Chlorine → HCID 86743247, compound

HRID 231960Notes

Reaction equation

HRID 231960 reaction equation
C(S[C@H:4]1[N:7]([C:8](=[C:22]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([S:38][C:39]3[CH:44]=[C:43]([Cl:45])[C:42]([Cl:46])=[CH:41][C:40]=3[Cl:47])=[O:37])=[CH:32][CH:31]=2)[C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[S:10])[C:6](=[O:48])[C@@H:5]1[C@H:49]([OH:51])[CH3:50])C.[Cl:52]Cl>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:52][C@@H:4]1[N:7]([C:8](=[C:22]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([S:38][C:39]3[CH:44]=[C:43]([Cl:45])[C:42]([Cl:46])=[CH:41][C:40]=3[Cl:47])=[O:37])=[CH:32][CH:31]=2)[C:23](=[O:28])[C:24]([CH3:25])([CH3:27])[CH3:26])[C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[S:10])[C:6](=[O:48])[C@@H:5]1[C@H:49]([OH:51])[CH3:50]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86743248HCID 86743248, compound

Product 1

HCID 86743247HCID 86743247, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1.26 g of 4-nitrobenzyl 2-[4(R)-ethylthio-3(S)-(1(R)-hydroxyethyl)-azetidin-2-on-1-yl]-3-[4-(2,4,5-trichlorophenylthio-(carbonyl))-phenoxy]-3-trimethylacetylthiopropenoate in 30 ml of dry chloroform at -40° C. was added a solution of 1.83 mmol chlorine in 4 ml of carbon tetrachloride, and the solution was stirred for 30 minutes. The reaction mixture was allowed to reach room temperature and evaporated to dryness. Chromatography of the residue (silica gel, hexane/ethyl acetate mixtures as eluant) gave the title compound as a pale yellow foam (0.706 g). νmax (CHCl3) 1784 cm-1.

Workup

  1. customto reach room temperature
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-a6bd51f1480e4d81bccb44be2b662022
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

Loading…