Chlorine → HCID 86742652, compound

HRID 2291298Notes

Reaction equation

HRID 2291298 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]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[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:45])[C@@H:5]1[C@H:46]([OH:48])[CH3:47])C.[Cl:49]Cl>C(Cl)(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:49][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]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[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:45])[C@@H:5]1[C@H:46]([OH:48])[CH3:47]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 86742653HCID 86742653, compound

Product 1

HCID 86742652HCID 86742652, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2.75 g of 4-nitrobenzyl 2-[4(R)-ethylthio-3(S)-(1(R)-hydroxyethyl)-azetidin-2-on-1-yl]-3-[4-(phenylthio-(carbonyl))-phenoxy]-3-trimethylacetylthiopropenoate in 25 ml of dry chloroform at -40° C. was added a solution of 5.3 mmol of chlorine in 7 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 (1.98 g)

Workup

  1. customto reach room temperature
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-576daefa01974e559966dc31673bd895
Source dataset
uspto-grants-1989_01
Patent number
US04795748

Reaction notes

Loading…