Water → Methyl 7-Phthalimido-3-methylenecepham-4-carboxylate

HRID 1679569Notes

Reaction equation

HRID 1679569 reaction equation
[C:1]1(=[O:26])[N:5]([CH:6]2[C:19](=[O:20])[N:8]3[CH:9]([C:15]([O:17][CH3:18])=[O:16])[C:10](=[CH2:14])[CH2:11][S:12](=O)[C@H:7]23)[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.CN(C)C=O.P(Cl)(Cl)Cl.O>C(OCC)(=O)C>[C:4]1(=[O:21])[N:5]([CH:6]2[C:19](=[O:20])[N:8]3[CH:9]([C:15]([O:17][CH3:18])=[O:16])[C:10](=[CH2:14])[CH2:11][S:12][C@H:7]23)[C:1](=[O:26])[C:2]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:3]12

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 69799987Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

Product 1

HCID 70604062Methyl 7-Phthalimido-3-methylenecepham-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

About one-half of the crude product from Example 14 was dissolved in 25 ml. of cold N,N-dimethylformamide. The solution was treated with 345 mg. (2.5 mmol.) of phosphorous trichloride, and the mixture was stirred in an ice bath for 30 minutes. The resulting reaction mixture then was poured into a mixture of water and ethyl acetate. The ethyl acetate solution was separated, washed with 5 percent hydrochloric acid and water, dried over magnesium sulfate and evaporated to dryness in vacuo. The nmr spectrum of the residue which was obtained was consistent with the structure of the title compound.

Workup

  1. additionThe solution was treated with 345 mg
  2. customThe resulting reaction mixture
  3. customThe ethyl acetate solution was separated
  4. washwashed with 5 percent hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customThe nmr spectrum of the residue which was obtained

Sources & evidence

ORD record
ord-ac4df894a56746d4aea3809ca03c147c
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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