1,5-Diazabicyclo(5,4,0)undec-5-ene → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester

HRID 1155446

反応式

HRID 1155446 の反応式
[C:1]1([CH:7]([O:14][C:15](=[O:50])/[C:16](/[N:21]2[CH:24]([S:25]S(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)[CH:23]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:22]2=[O:49])=[C:17](\[O:19][CH3:20])/[CH3:18])[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.C1(C(OC(=O)/C=C\C)C2C=CC=CC=2)C=CC=CC=1.N12CCCCC1C=NCCC2>O1CCCC1.C1C=CC=CC=1>[C:8]1([CH:7]([O:14][C:15]([CH:16]2[N:21]3[C:22](=[O:49])[C@@H:23]([NH:38][C:39](=[O:48])[CH2:40][O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C@H:24]3[S:25][CH:18]=[C:17]2[O:19][CH3:20])=[O:50])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 70527120Isocrotonic acid diphenylmethyl esterHCID 705571912-[4-(p-Nitrobenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester

生成物 1

HCID 705584137beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 367 mg (0.5 mM) of a mixture consisting of 2-[4-(p-nitrobenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-crotonic acid diphenylmethyl ester and the corresponding isocrotonic acid diphenylmethyl ester, and 152 mg (1.0 mM) of 1,5-diazabicyclo[5.4.0]undec-5-ene in 10 ml of dry tetrahydrofurane is stirred for 40 minutes at room temperature. The reaction mixture is diluted with benzene, washed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution, dried over sodium sulphate and freed from the solvent in vacuo. The residue is chromatographed on acid-washed silica gel, using toluene/ethyl acetate, 7:1, as the running agent, whereby pure 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester is obtained. Subsequent elution with toluene/ethyl acetate, 2:1, results in the isolation of a mixture which in addition to 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4-carboxylic acid diphenylmethyl ester also contains 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester.

後処理

  1. washwashed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution
  2. dry with materialdried over sodium sulphate
  3. customThe residue is chromatographed
  4. washon acid-washed silica gel

出典と根拠

ORDレコード
ord-e3ae79b427df45b4aa58f0d5c58810ca
出典データセット
uspto-grants-1981_11
特許番号
US04301278

関連ノート

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