Pyridine → O-benzhydryl (6R)-3-(1,3-benzoxazol-2-yl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate

HRID 974870

反応式

HRID 974870 の反応式
[NH2:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[S:19])=[C:6]([C:9]3[O:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH2:7][S:8][C@H:3]12.[C:36]([NH:55][C:56]1[S:57][CH:58]=[C:59](/[C:61](=[N:65]/[O:66][CH3:67])/[C:62](O)=[O:63])[N:60]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)Cl.O>[C:36]([NH:55][C:56]1[S:57][CH:58]=[C:59](/[C:61](=[N:65]/[O:66][CH3:67])/[C:62]([NH:1][CH:2]2[C:34](=[O:35])[N:4]3[C:5]([C:18]([O:20][CH:21]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[S:19])=[C:6]([C:9]4[O:10][C:11]5[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=5[N:13]=4)[CH2:7][S:8][C@H:3]23)=[O:63])[N:60]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 5928144(Z)-2-methoxymino-2-(2-(tritylamino)thiazol-4-yl)acetic acidHCID 131719875Diphenylmethyl 7-amino-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate

生成物 1

HCID 172974451O-benzhydryl (6R)-3-(1,3-benzoxazol-2-yl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

A 207 mg portion of diphenylmethyl 7-amino-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate was dissolved in 4 ml of methylene chloride and the resulting solution was cooled to -20° C. To this were added 213 mg of (Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoaceticacid, 0.13 ml of pyridine and 45 μl of phosphorous oxychloride, followed by 20 minutes of stirring at the same temperature. The resulting solution was mixed with 4 ml of water, stirred for additional 1 hour at room temperature, and then subjected to organic layer separation. After drying the resulting organic layer on anhydrous magnesium sulfate and distilling off the solvent under a reduced pressure, the residue was purified by a column chromatography (30 g silica gel, toluene:ethyl acetate =3:1) to obtain 272 mg of the title compound (yield, 72%).

後処理

  1. stirringstirred for additional 1 hour at room temperature
  2. customsubjected to organic layer separation
  3. dry with materialAfter drying the resulting organic layer on anhydrous magnesium sulfate
  4. distillationdistilling off the solvent under a reduced pressure
  5. customthe residue was purified by a column chromatography (30 g silica gel, toluene:ethyl acetate =3:1)

出典と根拠

ORDレコード
ord-f3e6386fd9e244d0bfa587380522b92f
出典データセット
uspto-grants-1997_03
特許番号
US05607927

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