2,6-Lutidine → p-Nitrobenzyl 2-chloro-2-(4-methylthio-2-azetidinon-1-yl)acetate

HRID 980960Notes

Reaction equation

N1C(C)=CC=CC=1C.S(Cl)([Cl:11])=O.O[CH:14]([N:28]1[CH:31]([S:32][CH3:33])[CH2:30][C:29]1=[O:34])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16]>O1CCCC1.C(OCC)(=O)C>[Cl:11][CH:14]([N:28]1[CH:31]([S:32][CH3:33])[CH2:30][C:29]1=[O:34])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16]

Participants

Conditions

Temperature: -20 °C

Procedure

2,6-Lutidine (626 mg) and thionyl chloride (695 mg) were successively added dropwise to a solution of p-nitrobenzyl 2-hydroxy-2-(4-methylthio-2-azetidinon-1-yl)acetate (1.59 g) in tetrahydrofuran (30 ml), whilst stirring at -20° C. The reaction mixture was stirred at -20° to -15° C. for 30 minutes, diluted with ethyl acetate, washed with water (once), neutralized with a dilute aqueous solution of sodium bicarbonate solution and further washed with water.

Workup

stirringThe reaction mixture was stirred at -20° to -15° C. for 30 minutes
washwashed with water (once),
washfurther washed with water

Sources & evidence

ORD record: ord-5eee7d0274934e50b674416f2652d524
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04639441

Reaction notes

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