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Water → 4-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 364550
ノート
印刷プレビュー

反応式

HRID 364550 の反応式
C[Si](CC(N)=O)(C)C.[NH2:9][CH:10]1[C:30](=[O:31])[N:12]2[C:13]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12.[CH:32]([NH:34][C:35]1[S:36][CH:37]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41](Cl)=[O:42])[N:39]=1)=[O:33].O>C(Cl)Cl>[CH:32]([NH:34][C:35]1[S:36][CH:37]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41]([NH:9][CH:10]2[C:30](=[O:31])[N:12]3[C:13]([C:17]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]23)=[O:42])[N:39]=1)=[O:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 537143512-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride

生成物 1

HCID 1317124414-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate収率 93.9%

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

N,N-Dimethylformamide (3 drops) was added to a suspension of 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 23 g.) in thionyl chloride (230 ml), and stirred at 60° C. for 5 minutes. After concentrating the solution in vacuo, benzene was added to the residue. The presipitates were collected by filtration, washed with benzene (30 ml.) three times and diethyl ether in turn to give 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 18 g.). On the other hand, trimethylsilylacetamide (46 g.) was added to a suspension of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (16.8 g.) in methylene chloride (168 ml.), and stirred at 40° C. for an hour. To the suspension was gradually added 2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetyl chloride (anti isomer, 13.6 g.) at -5° to 0° C., and stirred at the same temperature for an hour. Water (150 ml.) was added to the resultant solution and stirred for 15 minutes. The recipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyimino-acetamido]-3-cephem-4-carboxylate (anti isomer, 25.7 g.).

後処理

  1. customat -5° to 0° C.
  2. stirringstirred at the same temperature for an hour
  3. stirringstirred for 15 minutes
  4. filtrationThe recipitates were collected by filtration
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide under reduced pressure

出典と根拠

ORDレコード
ord-8a3a126a21e34d32a70d6bdec87e6803
出典データセット
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04604456

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート