Pyridine → HCID 70457302, compound

HRID 904098Notes

Reaction equation

HRID 904098 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(Cl)Cl>[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 6344DichloromethaneSolvent

Procedure

A solution of the triphenyl phosphite-chlorine reagent was prepared by bubbling chlorine through a solution of 2.89 ml (11 mmol) of triphenyl phosphite in 50 ml of methylene chloride at -15° C. To this solution was added 5.02 gm (10 mmol) of 4'-nitrobenzyl 7-phenoxy-acetamido-3-methyl-3-cephem-4-carboxylate and 0.85 ml (11.5 mmol) of pyridine. The reaction mixture was stirred for 1 hour at -15° to -10° C. after which time was added 6.0 ml (64.8 mmole) of isobutanol. The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature over a 2 hour period. The titled nucleus hydrochloride ester, which began to crystallize in about 15 minutes, was filtered, washed with methylene chloride, and dried. A total of 3.55 grams (92%) of the titled product was obtained as white crystals: m.p. 189° C. (decomp.).

Workup

  1. customThe cooling bath was removed
  2. customto crystallize in about 15 minutes
  3. filtrationwas filtered
  4. washwashed with methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-e847d4912f8b4d47b2abe07ff84c1261
Source dataset
uspto-grants-1980_10
Patent number
US04230644

Reaction notes

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