Hydrochloric Acid → benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

HRID 704268Notes

Reaction equation

HRID 704268 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:47][O:48][CH3:49])[C:10]([NH:12][CH:13]2[C:45](=[O:46])[N:15]3[C:16]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:17]([S:20]/[CH:21]=[CH:22]\[C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.O.C(=O)(O)[O-].[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:47][O:48][CH3:49])[C:10]([NH:12][CH:13]2[C:45](=[O:46])[N:15]3[C:16]([C:29]([O:31][CH:32]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:30])=[C:17]([S:20]/[CH:21]=[CH:22]\[C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 131716149benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

Product 1

HCID 131716152benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylateYield 89.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)-vinylthio]-3-cephem-4-carboxylate (syn isomer) (1 g) in a mixture of methanol (10 ml) and tetrahydrofuran (5 ml) was added conc. hydrochloric acid (0.31 ml) at ambient temperature and the mixture was stirred at the same temperature for 4 hours. To the reaction mixture were added water and ethyl acetate and the mixture was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (syn isomer) (0.86 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ff5ab13c4fa9461388fe6a115662fb8d
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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