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

HRID 2351144Notes

Reaction equation

HRID 2351144 reaction equation
C([NH:3][CH:4]1[C:36](=[O:37])[N:6]2[C:7]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:9][S:10][C@H:5]12)=O.Cl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO.O>[NH2:3][CH:4]1[C:36](=[O:37])[N:6]2[C:7]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:9][S:10][C@H:5]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 88631981benzhydryl 7-formamido-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

Product 1

HCID 67948113benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylateYield 79.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of benzhydryl 7-formamido-3 -[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (69.8 g) in methanol (350 ml) was added conc. hydrochloric acid (40.7 ml). The mixture was heated at 30°-35° C. for 2 hours. The mixture was poured into a mixture of ethyl acetate (2 l) and water (1 l) and adjusted to pH 6.5 with a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water and saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo to a crystal. The crystal was washed with diethyl ether to give benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (52.3 g).

Workup

  1. temperatureThe mixture was heated at 30°-35° C. for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous solution of sodium chloride in turn
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to a crystal
  6. washThe crystal was washed with diethyl ether

Sources & evidence

ORD record
ord-1b493b70545e4134ac08ab3c7cf59538
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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