Dimethylformamide → HCID 70559813, compound

HRID 1730306Notes

Reaction equation

HRID 1730306 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14](O)[CH2:15][S:16][C@H:11]12)=[O:8].CN(C=O)C.P(Br)(Br)[Br:39].C(OCC)(=O)C>O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([Br:39])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 70559813HCID 70559813, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 19 g. (40 mmole) of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate in 300 ml. of dry DMF was added 15 g. (56 mmole) of phosphorus tribromide and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water and the organic phase was separated and washed repeatedly with water and dried over magnesium sulfate. The dried organic phase was evaporated in vacuo todryness. The crude reaction product residue weighing about 9 g. was purified by chromatography over 500 g. of silica gel using ethyl acetate-hexane (55:45 v:v) as eluent. The eluate was evaporated to drynessunder reduced pressure and the product, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-bromo-3-cephem-4-carboxylate was obtained crystalline by the triturating the dry residue with diethyl ether.

Workup

  1. customthe organic phase was separated
  2. washwashed repeatedly with water
  3. dry with materialdried over magnesium sulfate
  4. customThe dried organic phase was evaporated in vacuo todryness
  5. customThe crude reaction product residue
  6. customwas purified by chromatography over 500 g
  7. customThe eluate was evaporated

Sources & evidence

ORD record
ord-22df993ca0be445ba19c2fad0d00422f
Source dataset
uspto-grants-1976_11
Patent number
US03992377

Reaction notes

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