Chlorine → HCID 131714648, compound

HRID 1381211Notes

Reaction equation

HRID 1381211 reaction equation
C(S[C@H:4]1[N:7]([C:8](=[C:22]([S:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[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:37])[C@@H:5]1[C@H:38]([OH:40])[CH3:39])C.[Cl:41]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Cl:41][C@H:4]1[N:7]([C:8](=[C:22]([S:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[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:37])[C@@H:5]1[C@H:38]([OH:40])[CH3:39]

Participants

5

Reactant 2

HCID 24526ChlorineHCID 131714649HCID 131714649, compound

Product 1

HCID 131714648HCID 131714648, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1 g of 4-nitrobenzyl 2-[4(R)-ethylthio-3(S)-{1(R)-hydroxyethyl}-azetidin-2-on-1-yl]-3-(4-methylthiophenoxy)-3-trimethylacetylthio-propenate in dichloromethane at -40° was added a solution of 1.6 mmol of chlorine in carbon tetrachloride. After 30 minutes the reaction was warmed to room temperature and evaporated to dryness. Chromatography over silica gel and elution with hexane-ethyl acetate mixtures afforded the title compound as a pale yellow foam (0.66 g, 68%).

Workup

  1. customevaporated to dryness
  2. washChromatography over silica gel and elution with hexane-ethyl acetate mixtures

Sources & evidence

ORD record
ord-8b13ecc5ec5244e6820cf94e651d5195
Source dataset
uspto-grants-1986_04
Patent number
US04585767

Reaction notes

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