Aluminum(III) Chloride → HCID 70547055, compound

HRID 971519Notes

Reaction equation

HRID 971519 reaction equation
C1(CO[C:6]([S:8][CH:9]2[N:12]([C:13](=[C:22]([OH:25])CBr)[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[C:11](=[O:26])[CH:10]2[NH:27][C:28](=[O:37])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[O:30]([CH2:29][C:28]([NH:27][CH:10]1[C:11](=[O:26])[N:12]2[CH:13]([C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:21])[Cl:20])=[O:15])[C:22](=[O:25])[CH2:6][S:8][C@H:9]12)=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 867355482,2,2-Trichloroethyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)-acetate

Product 1

HCID 70547055HCID 70547055, compoundYield 124.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (330 mg) in methylene chloride (6 ml) is added aluminum chloride (330 mg) at room temperature, and the mixture is stirred for 60 minutes. The reaction mixture is poured into ice cold diluted hydrochloric acid, and is extracted with ethyl acetate. The extract solution is washed with diluted hydrochloric acid and water, dried, and evaporated to give 2,2,2-trichloroethyl 7-phenoxyacetamido-3-oxocepham-4-carboxylate (300 mg). Foam. IR: vmaxCHCl3 3420, 1780, 1685 cm-1. NMR: δCDCl3 3.37s2H, 4.53s2H, 4.85s2H, 5.07d(4)1H, 5.20-5.73m2H, 6.8-7.7m6H.

Workup

  1. additionThe reaction mixture is poured into ice cold diluted hydrochloric acid
  2. extractionis extracted with ethyl acetate
  3. washThe extract solution is washed with diluted hydrochloric acid and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e95bf9781ebb4da88465914a34657990
Source dataset
uspto-grants-1979_07
Patent number
US04160085

Reaction notes

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