Chlorine → HCID 86743253, compound

HRID 231969Notes

Reaction equation

HRID 231969 reaction equation
[C:1]([C:4]1[CH:42]=[CH:41][C:7]([O:8][C:9]([C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[C:10]([N:24]2[C@H:27](SCC)[C@@H:26]([C@H:31]([OH:33])[CH3:32])[C:25]2=[O:34])[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[S:12])=[CH:6][CH:5]=1)([OH:3])=[O:2].[Cl:43]Cl>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[C:1]([C:4]1[CH:42]=[CH:41][C:7]([O:8][C:9]([C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[C:10]([N:24]2[C@@H:27]([Cl:43])[C@@H:26]([C@H:31]([OH:33])[CH3:32])[C:25]2=[O:34])[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[S:12])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86743251HCID 86743251, compound

Product 1

HCID 86743253HCID 86743253, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 10 g of 4-nitrobenzyl 3-(4-carboxyphenoxy)-2-(4(R)-ethylthio-3(S)- [1(R)-hydroxyethyl]azetidin-2-on-1-yl)-3-trimethylacetylthiopropenoate in 60 ml of chloroform at -60° C. was added a solution of 192 mmoles of chlorine in 17.8 ml of carbon tetrachloride. After 30 minutes, the reaction mixture was left to warm to room temperature, and the solvent was then removed in vacuo. Chromatography over silica gel using hexane-ethyl acetate-formic acid mixtures afforded 7.3 g of the title compound as a pale yellow foam.

Workup

  1. waitthe reaction mixture was left
  2. customthe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-3b49b9003d694f6894dfdbd6ddcc4813
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

Loading…