Pyridine → HCID 70457302, compound

HRID 904099Notes

Reaction equation

HRID 904099 reaction equation
[Cl:1][Cl:2].[P:3]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.C(O)C(C)C>O1CCCC1>[P:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:1][Cl:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6560IsobutanolHCID 7540Triphenyl phosphiteHCID 24526Chlorine

Product 1

HCID 70457302HCID 70457302, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of the triphenyl phosphite-chlorine reagent was prepared by bubbling chlorine into a solution of 11 mmol of triphenyl phosphite in tetrahydrofuran (THF) at -10° C. To the solution was added 4.84 gm (10 mmol) of 4'-nitrobenzyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate. Subsequently 0.95 ml (11 mmol) of pyridine was added to the reaction mixture. The reaction was then allowed to stir at -10° C. for 1 hour after which time it was allowed to warm to room temperature and stir for another 2 hours. Then 6.0 ml (65 mmol) of isobutanol was added. After 2 hours the reaction mixture was filtered. The crystalline nucleus hydrochloride ester thereby obtained was washed with THF and dried affording 3.03 gm (78.5%): m.p. 151-153° C. (decomp.).

Workup

  1. temperatureto warm to room temperature
  2. stirringstir for another 2 hours
  3. filtrationAfter 2 hours the reaction mixture was filtered

Sources & evidence

ORD record
ord-1b1524d30d024d90b8c82f7daa3e097c
Source dataset
uspto-grants-1980_10
Patent number
US04230644

Reaction notes

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