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

HRID 1155822Notes

Reaction equation

HRID 1155822 reaction equation
C([S:11][CH:12]1[N:15]([C:16](=[C:30]([OH:33])[CH2:31][Br:32])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:34])[CH:13]1[NH:35][C:36](=[O:45])[CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(OCC1C=CC=CC=1)=O.[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[SH:11][CH:12]1[N:15]([C:16](=[C:30]([OH:33])[CH2:31][Br:32])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:34])[CH:13]1[NH:35][C:36](=[O:45])[CH2:37][O:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375Nitromethane2×HCID 6451240Aluminum(III) ChlorideHCID 76184939HCID 76184939, compound

Product 1

HCID 86735550p-Nitrobenzyl alpha-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of p-nitrobenzyl α-[4-carbobenzoxythio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (480 mg) in methylene chloride (5 ml) containing 20% of nitromethane is added a solution of aluminum chloride (270 mg) in methylene chloride containing 20% of nitromethane (4 ml), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is poured into diluted hydrochloric acid, and is extracted with methylene chloride. The extract solution is washed water, dried over magnesium sulfate, and evaporated to give p-nitrobenzyl α-[4-mercapto-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (376 mg). Yield: 99.5%.

Workup

  1. extractionis extracted with methylene chloride
  2. washThe extract solution is washed water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-820e221f072644ab87c3615282e07fa2
Source dataset
uspto-grants-1982_06
Patent number
US04332722

Reaction notes

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