Pyridine → Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochloride

HRID 1154204Notes

Reaction equation

HRID 1154204 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].N1C=CC=CC=1.C(OC(C(NC(OCC)=O)CCCC([NH:35][CH:36]1[C:61](=[O:62])[N:38]2[C:39]([C:45]([O:47][CH:48]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:46])=[C:40]([CH:43]=[CH2:44])[CH2:41][S:42][C@H:37]12)=O)=O)(C1C=CC=CC=1)C1C=CC=CC=1.COCCO>C(Cl)CCl.O>[ClH:2].[NH2:35][CH:36]1[C:61](=[O:62])[N:38]2[C:39]([C:45]([O:47][CH:48]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:46])=[C:40]([CH:43]=[CH2:44])[CH2:41][S:42][C@H:37]12

Participants

7

Reactant 4

HCID 1049PyridineHCID 80192-MethoxyethanolHCID 24819Phosphorus pentachlorideHCID 14099864Benzhydryl 7-(5-benzhydryloxycarbonyl-5-ethoxycarbonylaminopentanamido)-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 12818005Benzhydryl 7-amino-3vinyl-3cephem-4-carboxylate hydrochlorideYield 36.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of phosphorus pentachloride (7.87 g) in ethylene chloride (47.75 ml) was added pyridine (2.99 g) at 5° to 6° C. After stirring for 30 minutes, to the mixture was added benzhydryl 7-(5-benzhydryloxycarbonyl-5-ethoxycarbonylaminopentanamido)-3-vinyl-3-cephem-4-carboxylate (9.75 g). After stirring for 2 hours at 5° to 6° C. and cooling to -30° to -20° C., the mixture was treated with 2-methoxyethanol (7.67 ml) for 1.5 hours and then with water (10 ml) for an hour. The precipitates were collected by filtration and washed with ethyl acetate and diisopropyl alcohol to give benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (1.99 g).

Workup

  1. stirringAfter stirring for 2 hours at 5° to 6° C.
  2. temperaturecooling to -30° to -20° C.
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with ethyl acetate and diisopropyl alcohol

Sources & evidence

ORD record
ord-00924d8bbb2741c99053889196764c22
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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