Diazomethane → Diphenylmethyl (6R-trans)-3-methoxy-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

HRID 1388960Notes

Reaction equation

HRID 1388960 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[OH:37])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:40])=[N-]>CO>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[O:37][CH3:40])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 547082513-Hydroxy-7beta-phenoxyacetylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

Product 1

HCID 6453042Diphenylmethyl (6R-trans)-3-methoxy-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The resulting 7β-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid diphenylmethyl ester is taken up in methanol and treated, at 0° C., with an excess of an ethereal solution of diazomethane. After a reaction time of 5 minutes, the solution is concentrated completely and the oily residue is chromatographed on silica gel thick layer plates (toluene/ethyl acetate, 3:1). The silica gel in the zone at Rf=0.19 is extracted with ethyl acetate and gives 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester; melting point 120° C. (from ether), IR spectrum (in CHCl3); 3310, 1775, 1700, 1690 and 1600 cm-1.

Workup

  1. additiontreated, at 0° C.
  2. concentrationAfter a reaction time of 5 minutes, the solution is concentrated completely
  3. customthe oily residue is chromatographed on silica gel thick layer plates (toluene/ethyl acetate, 3:1)
  4. extractionThe silica gel in the zone at Rf=0.19 is extracted with ethyl acetate

Sources & evidence

ORD record
ord-89922b4bac9740d9a7af267792c8d1b4
Source dataset
uspto-grants-1984_02
Patent number
US04434287

Reaction notes

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