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

HRID 1679225Notes

Reaction equation

HRID 1679225 reaction equation
[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27](N3CCOCC3)[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:36])[CH:10]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:7])[CH2:3][CH2:2]1.Cl.C[OH:50]>C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27]([OH:50])[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:36])[CH:10]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 53903289HCID 53903289, compound

Product 1

HCID 86735549p-Nitrobenzyl alpha-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-alpha-(2-bromo-1-hydroxyethylidene)acetateYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-[2-bromo-1-(morpholin-4-yl)ethylidene]acetate (300 mg) in a mixture of methanol (22 ml) and methylene chloride (3.5 ml), and the mixture is stirred at room temperature under nitrogen atmosphere after addition of 10% hydrochloric acid (4ml). After 2 hours, the reaction mixture is poured into ice water, and is extracted with chloroform. The extract solution is washed with water, dried, and evaporated to give p-nitrobenzyl 4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxo-α-(2-bromo-1-hydroxyethylidene)azetidine-1-acetate (252 mg). Foam. Yield: 92.8%. IR: νmaxCHCl3 3426, 1781, 1710, 1690, 1601 cm-1. NMR: δCDCl3 0.23-1.33m5H, 3.84-4.36m4H, 4.55s2H, 5.10-5.32m3H, 5.88(5Hz)1H, 6.83-8.33m9H, 12.0s1H.

Workup

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

Sources & evidence

ORD record
ord-b8dd158c027e467090c5a677ced44261
Source dataset
uspto-grants-1978_03
Patent number
US04079181

Reaction notes

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