Carbon tetrabromide → Benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate

HRID 2413813Notes

Reaction equation

HRID 2413813 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[C:25]1([CH2:31][C:32]([NH:34][CH:35]2[C:60](=[O:61])[N:37]3[CH:38]([C:44]([O:46][CH:47]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:45])[C:39]([CH:42]=O)=[CH:40][S:41][C@H:36]23)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.[Zn].C(OCC)(=O)C>[C:25]1([CH2:31][C:32]([NH:34][CH:35]2[C:60](=[O:61])[N:37]3[CH:38]([C:44]([O:46][CH:47]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[O:45])[C:39]([CH:42]=[C:20]([Br:24])[Br:21])=[CH:40][S:41][C@H:36]23)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 88626080HCID 88626080, compound

Product 1

HCID 88600993Benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylateYield 33.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of triphenylphosphine (40.7 g) and zinc powder (18.5 g) in methylene chloride (250 ml) was added carbontetrabromide (45 g) at 20°-30° C. Benzhydryl 7-phenylacetamido-3-formyl-2-cephem-4-carboxylate (10 g) was added portionwise to the above reaction mixture, and the mixture was stirred for 30 minutes at room temperature. Triphenylphosphine oxide was solidified by addition of ethyl acetate to the reaction mixture and removed by filtration. The residue left by removal of the solvents was chromatographed on silica gel. The elution with chloroform containing ethyl acetate (10%) gave benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate (4.4 g).

Workup

  1. customremoved by filtration
  2. waitThe residue left by removal of the solvents
  3. customwas chromatographed on silica gel
  4. washThe elution with chloroform
  5. additioncontaining ethyl acetate (10%)

Sources & evidence

ORD record
ord-b0040f1cab25468493caf6878cc7dd83
Source dataset
uspto-grants-1988_01
Patent number
US04719206

Reaction notes

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