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Hydrochloric Acid → Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

HRID 1247920
ノート
印刷プレビュー

反応式

HRID 1247920 の反応式
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12.CN(C)C1C=CC=CC=1.Cl.[CH2:40]([O:42][N:43]=[C:44]([C:48]1[N:52]=[C:51]([NH2:53])[S:50][N:49]=1)[C:45](Cl)=[O:46])[CH3:41].Cl>C(Cl)Cl.O>[CH2:40]([O:42][N:43]=[C:44]([C:48]1[N:52]=[C:51]([NH2:53])[S:50][N:49]=1)[C:45]([NH:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12)=[O:46])[CH3:41]
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

7

反応物 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 13239629Benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochlorideHCID 867392542-Ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride

生成物 1

HCID 131714229Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate
収率 88.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

To a suspension of diphenylmethyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (27 g) in methylene chloride (300 ml) was added N,N-dimethylaniline (36.2 g) under cooling in an ice bath at 5° C. To the solution was added portionwise 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (syn isomer) (16.2 g) below 11° C. and the mixture was stirred for 45 minutes at 5° C. The reaction mixture was diluted with a mixed solvent of methylene chloride (100 ml) and water (200 ml) and adjusted to pH 2 with 1N hydrochloric acid. The organic layer was separated out, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was triturated in diethyl ether to give diphenylmethyl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (32.4 g), mp 120° to 125° C. (dec.).

後処理

  1. customThe organic layer was separated out
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was triturated in diethyl ether

出典と根拠

ORDレコード
ord-a11c7bfbbb7e41bb9ba9a637defe5c84
出典データセット
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04521413

反応ノート

読み込み中…

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