Acetic Acid → HCID 178452985、化合物

HRID 249600ノート

反応式

HRID 249600 の反応式
[C:1]([S:9][CH2:10][S:11][C:12]1[N:13]=[N:14][NH:15][CH:16]=1)(=O)[C:2]1C=CC=CC=1.[CH3:17][O-:18].[Na+].C1(C(OC([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39]CC=2OS(C)(=O)=O)=O)C2C=CC=CC=2)C=CC=CC=1.[C:88](O)(=O)[CH3:89].[CH3:92][OH:93]>CN(C)C=O.O>[C:50]1([CH:17]([O:18][C:92]([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:78])([CH3:80])[CH3:79])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39][CH2:2][C:1]=2[S:9][CH2:10][S:11][C:12]2[N:13]=[N:14][NH:15][CH:16]=2)=[O:93])[C:89]2[CH:88]=[CH:72][CH:68]=[CH:46][CH:45]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 887MethanolHCID 10260338benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-3-methylsulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 10942334Sodium MethoxideHCID 178526204HCID 178526204、化合物

生成物 1

HCID 178452985HCID 178452985、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 4-benzoylthiomethylthio-1,2,3-triazole (150 mg: 0.60 mMol.) in dimethylformamide (3 ml) at -60° C. is added a solution of sodium methoxide in methanol (1.26N: 0.95 ml), and the mixture is stirred for 80 minutes at -50° to -60° C. to the mixture at -7020 C. is added a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2trityloxyiminoacetamido]-3-methanesulfonyloxy-3-cephem-4carboxylic acid diphenylmethyl ester (485 mg : 0.5 mMol.) in dimethylformamide (2 ml) and the mixture is stirred at -70° C. for 20 minutes. The reaction mixture is mixed with acetic acid (0.1 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. The residue is crystallized from toluene to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol -4-yl)- 2-trityloxyiminoacetamido]-3-(1,2,3-triazol- 4-ylthiomethylthio)-3- cephem-4-carboxylic acid diphenylmethyl ester (227 mg) as colorless crystals. Yield : 44%.

後処理

  1. stirringthe mixture is stirred at -70° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized from toluene

出典と根拠

ORDレコード
ord-93e46678752647a5808edd2635ee4bca
出典データセット
uspto-grants-1993_05
特許番号
US05214037

反応ノート

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