Hydrochloric Acid → HCID 67948126, compound

HRID 704280Notes

Reaction equation

HRID 704280 reaction equation
C([NH:3][CH:4]1[C:37](=[O:38])[N:6]2[C:7]([C:21]([O:23][CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[N:18][CH:19]=3)[CH2:9][S:10][C@H:5]12)=O.Cl.O.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.O1CCCC1>[NH2:3][CH:4]1[C:37](=[O:38])[N:6]2[C:7]([C:21]([O:23][CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:22])=[C:8]([S:11]/[CH:12]=[CH:13]\[C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[N:18][CH:19]=3)[CH2:9][S:10][C@H:5]12

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 88528767HCID 88528767, compound

Product 1

HCID 67948126HCID 67948126, compoundYield 84.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of benzhydryl 7-formamido-3-[(Z)-2-(2-methyl-5-pyridyl)vinylthio]-3-cephem-4-carboxylate (17.5 g) in methanol (90 ml) was added conc. hydrochloric acid (10.0 ml) at ambient temperature and the mixture was stirred at 30° to 35° C. for 2.5 hours. The reaction mixture was poured into a mixture of cold water (250 ml), tetrahydrofuran (250 ml) and ethyl acetate (500 ml). The resultant mixture was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-amino-3-[(Z)-2-(2-methyl-5-pyridyl)vinylthio]-3-cephem-4-carboxylate (14.1 g).

Workup

  1. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-7dfc3239a42646d1bf3a2c43a8f8603d
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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