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

HRID 465176ノート

反応式

HRID 465176 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dba47a1025494ba4abe2bc294a77e1cf
出典データセット
uspto-grants-1985_10
特許番号
US04550162

反応ノート

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