Water → HCID 70559813, compound

HRID 1657740Notes

Reaction equation

HRID 1657740 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])=[CH:14][CH:15](O)[S:16][C@H:11]12)=[O:8].P(Br)(Br)[Br:34].C(OCC)(=O)C.O>CN(C=O)C>[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:34])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 70561434HCID 70561434, compound

Product 1

HCID 70559813HCID 70559813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 19 g. (40 mmole) of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-2-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 to dryness. 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 dryness under reduced pressure and the product, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-bromo-3-cephem-4-carboxylate was obtained crystalline by 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 to dryness
  5. customThe crude reaction product residue
  6. customwas purified by chromatography over 500 g
  7. customThe eluate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d307cb5b912946b595c3a8a7d2756c3e
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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