Hydrochloric Acid → Benzhydryl 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate

HRID 1262767Notes

Reaction equation

HRID 1262767 reaction equation
C([NH:3][C:4]1[S:5][C:6]([Cl:50])=[C:7]([C:9](=[N:40][O:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24][CH:25]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[S:23])=[C:17]([CH2:20][CH3:21])[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][C:6]([Cl:50])=[C:7]([C:9](=[N:40][O:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:10]([NH:12][CH:13]2[C:38](=[O:39])[N:15]3[C:16]([C:22]([O:24][CH:25]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[S:23])=[C:17]([CH2:20][CH3:21])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131713538Benzhydryl 7-[2-(2-formamido-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate

Product 1

HCID 131713546Benzhydryl 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylateYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzhydryl 7-[2-(2-formamido-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.7 g) in methanol (60 ml) was added conc. hydrochloric acid (1.5 ml) at 35° C. and the mixture was stirred for 90 minutes at the same temperature. The reaction mixture was adjusted to pH 6.0 with an aqueous solution of sodium bicarbonate. Methanol was evaporated under reduced pressure and the residue was dissolved into ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give benzhydryl 7-[2-(2-amino-5-chlorothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-ethylthio-3-cephem-4-carboxylate (syn isomer, 2.0 g), mp. 171° to 176° C.

Workup

  1. customMethanol was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved into ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be6787adba584a03a9c494f0ece14d68
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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