Pyridine → p-Nitrobenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride

HRID 461944Notes

Reaction equation

HRID 461944 reaction equation
O(CC([NH:11][CH:12]1[C:33](=[O:34])[N:14]2[CH:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.C(Cl)[Cl:36].N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(O)C(C)C>[ClH:36].[NH2:11][CH:12]1[C:33](=[O:34])[N:14]2[CH:15]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[O:21])[C:16](=[CH2:19])[CH2:17][S:18][C@H:13]12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 20837924p-Nitrobenzyl 7-Penoxyacetamido-3-methylenecepham-4-carboxylate

Product 1

HCID 70560152p-Nitrobenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochlorideYield 58%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

To a solution of 965 mg. (2 mmole) of p-nitrobenzyl 7-phenoxyacetamido-3-methylenecepham-4-carboxylate in 10 ml. of methylene chloride were added 175 mg of dry pyridine and 460 mg. of phosphorus pentachloride and the mixture was stirred at room temperature for 6 hours. One ml. of isobutanol was added to the mixture which was then stored at 0° C. overnight. The reaction product, p-nitrobenzyl 7-amino-3-methylenecepham-4-carboxylate hydrochloride, which formed as a crystalline precipitate was filtered to yield 430 mg. (58% yield).

Sources & evidence

ORD record
ord-cf7963311b594808b2d63d41a09628fd
Source dataset
uspto-grants-1977_12
Patent number
US04064343

Reaction notes

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