Pyridine → 4-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

HRID 1414129Notes

Reaction equation

HRID 1414129 reaction equation
S1C=CC=C1CC([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([Cl:17])[CH2:15][S:16][C@H:11]12)=O.C(Cl)Cl.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>C(O)C(C)C>[ClH:17].[NH2:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=3)=[O:19])=[C:14]([Cl:17])[CH2:15][S:16][C@H:11]12

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24819Phosphorus pentachlorideHCID 705589584-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 703621504-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

To a solution of 500 mg. of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate in 6 ml. of methylene chloride was added 95 mg. of dry pyridine and 237 mg. of phosphorus pentachloride. The reaction mixture was stirred at room temperature for 1.5 hours, was thereafter cooled in an ice-water bath to about 5° C. and 0.6 ml. of iso-butyl alcohol were added. On continued cooling and stirring the reaction product, p-nitrobenzyl 7-amino-'-chloro-3-cephem-4-carboxylate hydrochloride, crystallized from the reaction mixture. The product was filtered, washed with cold methylene chloride and dried to yield 200 mg. of the crystalline product melting with decomposition at about 168° C.

Workup

  1. temperaturewas thereafter cooled in an ice-water bath to about 5° C.
  2. temperatureOn continued cooling
  3. customcrystallized from the reaction mixture
  4. filtrationThe product was filtered
  5. washwashed with cold methylene chloride
  6. customdried
  7. customto yield 200 mg
  8. custommelting with decomposition at about 168° C.

Sources & evidence

ORD record
ord-510af2f01b114900812bc27978ef2076
Source dataset
uspto-grants-1981_02
Patent number
US04252950

Reaction notes

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