Chlorine → p-Nitrobenzyl 2-(4-chloro-2-oxo-1-azetidinyl)-4,4-dimethyl-3-oxopentanoate

HRID 1031044Notes

Reaction equation

C(S[CH:6]1[N:9]([CH:10]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[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)=[O:12])[C:8](=[O:30])[CH2:7]1)(C)(C)C.[Cl:31]Cl>C(Cl)Cl.C(Cl)(Cl)(Cl)Cl>[Cl:31][CH:6]1[N:9]([CH:10]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[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)=[O:12])[C:8](=[O:30])[CH2:7]1

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 439 mg (1.0 mmol) of p-nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-4,4-dimethyl-3-oxopentanoate in 20 ml of dry methylene chloride is cooled to -50° C. and a solution of 166 mg of chlorine in 1.6 ml of carbon tetrachloride is added. After stirring for 30 minutes at -50° C., the solvent is evaporated in vacuo and the residue is recrystallized from methylene chloride/hexane, the product (348 mg) being obtained as a crystalline solid as a 6:4 mixture of the two diastereomeric title compounds.

Workup

customthe solvent is evaporated in vacuo
customthe residue is recrystallized from methylene chloride/hexane

Sources & evidence

ORD record: ord-aed38769fca24f7aafd6a3e1e02050d9
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108747

Reaction notes

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