Hydrochloric Acid → p-Nitrobenzyl 3-hyroxy-7-phenoxyacetamido-3-cephem-4-carboxylate

HRID 67849Notes

Reaction equation

HRID 67849 reaction equation
C1(CO[C:6]([S:8][CH:9]2[N:12]([C:13](=C(N3CCOCC3)CBr)[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)CC1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:52][OH:53].Cl>C(Cl)Cl>[OH:53][C:52]1[CH2:6][S:8][C@@H:9]2[CH:10]([NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:11](=[O:36])[N:12]2[C:13]=1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6451240Aluminum(III) ChlorideHCID 53903289HCID 53903289, compound

Product 1

HCID 67616247p-Nitrobenzyl 3-hyroxy-7-phenoxyacetamido-3-cephem-4-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-[2-bromo-1-(morpholin-4-yl)ethylidene]acetate (151 mg) in methylene chloride (1.5 ml) is added aluminum chloride (42 mg), and the mixture is stirred for 50 minutes under ice cooling. The mixture is diluted with ice water (2 ml), stirred for 5 minutes, and stirred with a mixture (15 ml) of methanol and methylene chloride (5:1) after addition of 10% hydrochloric acid (3 ml) at room temperature for 80 minutes. The reaction mixture is diluted with ice water, and is extracted with chloroform. The extract solution is washed with water, dried over magnesium sulfate, and evaporated to give p-nitrobenzyl 3-hydroxy-7-phenoxyacetamido-3-cephem-4-carboxylate (63 mg). Yield: 63%. This product is identical with the product of Example 4-III (3) produced by hydrolysis of the 4-morpholino group to be replaced with the corresponding hydroxy group.

Workup

  1. stirringstirred for 5 minutes
  2. extractionis extracted with chloroform
  3. washThe extract solution is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-31918e0dbb72493f88e9783a21987c4f
Source dataset
uspto-grants-1982_08
Patent number
US04346218

Reaction notes

Loading…