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

HRID 26103Notes

Reaction equation

HRID 26103 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.CCOCC>[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

5

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 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The resulting crude 7β-phenoxyacetamido-3-hydroxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is dissolved in methanol and a solution of diazomethane in ether is added at 0° C. After 10 minutes, the solution is carefully concentrated and the residue is dried under a high vacuum. The residue is purified by thick layer chromatography (toluene/ethyl acetate, 3:1, silica gel). After eluting the silica gel of the zone at Rf = 0.17 with ethyl acetate, and concentrating the solution on a rotary evaporator, 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester is obtained; melting point 120° C. (from ether).

Workup

  1. concentrationthe solution is carefully concentrated
  2. customthe residue is dried under a high vacuum
  3. customThe residue is purified by thick layer chromatography (toluene/ethyl acetate, 3:1, silica gel)
  4. washAfter eluting the silica gel of the zone at Rf = 0.17 with ethyl acetate
  5. concentrationconcentrating the solution
  6. customon a rotary evaporator

Sources & evidence

ORD record
ord-33ed86bd9a78465cbe69139ce8a64073
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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