Hydrochloric Acid → p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

HRID 1155818Notes

Reaction equation

HRID 1155818 reaction equation
C1(COC([S:8][CH:9]2[N:12]([C:13](=[C:27]([OH:30])[CH2:28][Br:29])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:31])[CH:10]2[NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CO>[SH:8][CH:9]1[N:12]([C:13](=[C:27]([OH:30])[CH2:28][Br:29])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C:11](=[O:31])[CH:10]1[NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 86735549p-Nitrobenzyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetate

Product 1

HCID 86735550p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetateYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (218 mg) in methanol free methylene chloride (2.1 ml) is added aluminum chloride (220 mg) under ice cooling, and the mixture is stirred under argon atmosphere. After 35 minutes, the reaction mixture is poured into ice water containing 4 N-hydrochloric acid (4 ml), stirred for 10 minutes, and is extracted with chloroform. The extract solution is washed with water, dried and evaporated to give p-nitrobenzyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (150 mg). Yellow foam. Yield: 94.6%. IR: νmaxCHCl3 3400, 1780, 1692, 1610, 1603 cm-1. NMR: δCDCl3 2.25d(10 Hz)1H, 4.25d(2 Hz)2H, 4.58s2H, 5.20-5.37m4H, 6.84-8.24m9H, 12.1s1H.

Workup

  1. stirringstirred for 10 minutes
  2. extractionis extracted with chloroform
  3. washThe extract solution is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-55a975a74c994672a58cb4bb3d8da12a
Source dataset
uspto-grants-1982_06
Patent number
US04332722

Reaction notes

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