Pyridine → HCID 70457302, compound

HRID 904100Notes

Reaction equation

HRID 904100 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>C(#N)C>[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 6342AcetonitrileSolvent

Procedure

A solution of the triphenyl phosphite-chlorine reagent was prepared by bubbling chlorine into a solution of about 11 mmol of triphenyl phosphite in 45 ml of acetonitrile at -10° C. To this solution was added 4.84 gm (10 mmol) of 4'-nitrobenzyl 7 -phenoxyacetamido-3-methyl-3-cephem-4-carboxylate and subsequently 0.95 ml (11 mmol) of pyridine at -10° C. After the reaction mixture was allowed to stir for 2 hours at -10° C. the ice bath was removed. After an additional 2 hours, 6.0 ml (65 mmol) of isobutanol was added to the reaction mixture. With seeding the product crystallized, and after stirring for 1 hour, it was filtered, washed with acetonitrile, and dried. Total yield 2.55 gm (66 .l%): m.p. 184° C. (decomp.).

Workup

  1. customwas removed
  2. customcrystallized
  3. filtrationit was filtered
  4. washwashed with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-8f940584c87a4405a64a1540db9a5e2d
Source dataset
uspto-grants-1980_10
Patent number
US04230644

Reaction notes

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