Hydrochloric Acid → HCID 131713545, compound

HRID 1262766Notes

Reaction equation

HRID 1262766 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:39][O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:10]([NH:12][CH:13]2[C:37](=[O:38])[N:15]3[C:16]([C:21]([O:23][CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[S:22])=[C:17]([CH3:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:39][O:40][CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:10]([NH:12][CH:13]2[C:37](=[O:38])[N:15]3[C:16]([C:21]([O:23][CH:24]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[S:22])=[C:17]([CH3:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131713537HCID 131713537, compound

Product 1

HCID 131713545HCID 131713545, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer, 2.3 g) in methanol (69 ml) was added conc. hydrochloric acid (1.44 ml) at 35° C., and the suspension was stirred for an hour at the same temperature. The reaction mixture was adjusted to pH 7.0 with an aqueous saturated solution of sodium bicarbonate. Methanol as evaporated in vacuo, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo to give benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer, 1.76 g). mp. 148°-155° C.

Workup

  1. customMethanol as evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-942e15fda72b4de58b270bb44b935080
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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