Water → p-Nitrobenzyl 7-Penoxyacetamido-3-methylenecepham-4-carboxylate

HRID 1679571Notes

Reaction equation

HRID 1679571 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:16](=[CH2:20])[CH2:17][S:18](=O)[C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.P(Cl)(Cl)Cl.O>C(OCC)(=O)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=3)=[O:22])[C:16](=[CH2:20])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 12780262p-Nitrobenzyl 7-Phenoxyacetamido-3-methylenecepham-4-carboxylate-1-oxide

Product 1

HCID 20837924p-Nitrobenzyl 7-Penoxyacetamido-3-methylenecepham-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

About one-half of the product from Example 17 was dissolved in 25 ml. of dry N,N-dimethylformamide. The mixture was cooled in an ice bath, and 370 mg. (2.7 mmol.) of phosphorous trichloride were added. The mixture was stirred with cooling for 30 minutes. The mixture then was poured into a mixture of water and ethyl acetate. The ethyl acetate solution was separated, washed successively with 5 percent hydrochloric acid and brine, dried over magnesium sulfate, and evaporated to dryness in vacuo. The residue (350 mg.) was consistent by nmr analysis with the structure of the title compound.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. temperaturewith cooling for 30 minutes
  3. customThe ethyl acetate solution was separated
  4. washwashed successively with 5 percent hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2121d4d0d6934120ae8a467dc839785c
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

Loading…