Hydrochloric Acid → 2,2,2-Trichloroethyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)-acetate

HRID 325473Notes

Reaction equation

HRID 325473 reaction equation
[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:22](N3CCCCC3)[CH2:23][Br:24])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[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:7])[CH2:3][CH2:2]1.Cl.C[OH:45]>>[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:22]([OH:45])[CH2:23][Br:24])[C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:20])[Cl:21])=[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:7])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 539863422,2,2-Trichloroethyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-[2-bromo-1-(piperidin-1-yl)ethylidene]acetate

Product 1

HCID 867355482,2,2-Trichloroethyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)-acetateYield 83.5%

Procedure

To a solution of 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-[2-bromo-1-(piperidin-1-yl)ethylidene]acetate (573 mg) in methanol (30 ml) is added 10% hydrochloric acid (7 ml), and the mixture is stirred at room temperature or at 40° to 45° C. After 30 minutes, the reaction mixture is poured into ice water, and is extracted with benzene. The extract solution is washed with water, dried, and evaporated to give 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(2-bromo-1-hydroxyethylidene)-acetate (434 mg). Yield: 83.5%. IR: νmaxCHCl3 3450, 1790, 1720, 1720 (sh), 1700 cm-1. NMR: δCDCl3 0.1-1.4m7H, 3.98d(7 Hz)2H, 4.27d(5 Hz)2H, 4.57s2H, 4.82d(3 Hz)2H, 5.27d(6;8 Hz)1H, 5.93d(5 Hz)1H, 6.8-7.5m6H, 11.67bra1H.

Workup

  1. extractionis extracted with benzene
  2. washThe extract solution is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-bdf93efeae4541d094ac801ed1f63f11
Source dataset
uspto-grants-1984_04
Patent number
US04440683

Reaction notes

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