Bromine → p-Nitrobenzyl 2-(4-bromo-2-azetidinon-1-yl)-2-(4-hydroxy-1,3-dithiolan-2-ylidene)acetate

HRID 980967Notes

Reaction equation

HRID 980967 reaction equation
[OH:1][CH:2]1[CH2:6][S:5][C:4](=[C:7]([N:21]2[CH:24](SC)[CH2:23][C:22]2=[O:27])[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:9])[S:3]1.[Br:28]Br>O1CCCC1.C(Cl)(Cl)(Cl)Cl>[Br:28][CH:24]1[N:21]([C:7](=[C:4]2[S:3][CH:2]([OH:1])[CH2:6][S:5]2)[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[O:9])[C:22](=[O:27])[CH2:23]1

Participants

5

Reactant 2

HCID 24408BromineHCID 86741253p-Nitrobenzyl 2-(4-hydroxy-1,3-dithiolan-2-ylidene)-2-(4-methylthio-2-azetidinon-1-yl)acetate

Product 1

HCID 53688010p-Nitrobenzyl 2-(4-bromo-2-azetidinon-1-yl)-2-(4-hydroxy-1,3-dithiolan-2-ylidene)acetateYield 99.8%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl 2-(4-hydroxy-1,3-dithiolan-2-ylidene)-2-(4-methylthio-2-azetidinon-1-yl)acetate (121 mg) was dissolved in tetrahydrofuran (1 ml). A solution of bromine (45.2 mg) in carbon tetrachloride was added dropwise to the resulting solution, with ice cooling. The mixture was stirred at that temperature for 10 minutes and then the solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (eluent: a 1:1 by volume mixture of benzene and ethyl acetate), to give 130 mg of the desired product.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe resulting residue was purified by column chromatography (eluent
  3. additiona 1:1 by volume mixture of benzene and ethyl acetate),

Sources & evidence

ORD record
ord-d83e03a6e9cd4fba955ff93dc999ff0c
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

Loading…