Acetic Anhydride → 5-[1-(2-Acetylaminothiazol-4-yl)-1-ethoxycarbonylmethylene]-2,4-dioxothiazolidine-3-acetic acid

HRID 2107174ノート

反応式

HRID 2107174 の反応式
[CH2:1]([O:3][C:4]([C:6]([CH:23]1[S:27][C:26](=[O:28])[N:25]([CH2:29][C:30]([OH:32])=[O:31])[C:24]1=[O:33])(O)[C:7]1[N:8]=[C:9]([NH:12][C:13](NC2C=CC=CC=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2].[C:34]1(NC(=O)NC2SC=C(C(=O)C(OCC)=O)N=2)C=CC=CC=1.O=C1N(CC(O)=O)C(=O)CS1.N1CCCCC1.C(OC(=O)C)(=O)C>O.N1C=CC=CC=1.C(O)C>[C:13]([NH:12][C:9]1[S:10][CH:11]=[C:7]([C:6](=[C:23]2[S:27][C:26](=[O:28])[N:25]([CH2:29][C:30]([OH:32])=[O:31])[C:24]2=[O:33])[C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:8]=1)(=[O:14])[CH3:34]

参加物

9

反応物 5

HCID 7918Acetic AnhydrideHCID 8082PiperidineHCID 2770836(2,4-Dioxo-1,3-thiazolidin-3-yl)acetic acidHCID 15053489Ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylateHCID 230475735-{1-Ethoxycarbonyl-1-hydroxy-1-[2-(3-phenylureido)thiazol-4-yl]methyl}-2,4-dioxothiazolidine-3-acetic acid

生成物 1

HCID 539168005-[1-(2-Acetylaminothiazol-4-yl)-1-ethoxycarbonylmethylene]-2,4-dioxothiazolidine-3-acetic acid

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

A mixture comprising 0.6 g of crude 5-{1-ethoxycarbonyl-1-hydroxy-1-[2-(3-phenylureido)thiazol-4-yl]methyl}-2,4-dioxothiazolidine-3-acetic acid [prepared from 2.6 g of ethyl 2-(3-phenylureido)thiazol-4-ylglyoxylate, 1.2 g of 2,4-dioxothiazolidine-3-acetic acid, 1.2 g of piperidine and 30 ml of ethanol by a procedure similar to that of Example 24], 0.5 g of acetic anhydride and 4 ml of pyridine was heated at 60° C. for 17 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated off under reduced pressure. The resulting oil was purified by silica gel column chromatography, using as eluent a 8:2:0.5 to 7:3:0.5 by volume mixture of benzene ethyl acetate and acetic acid, giving the desired compound as a yellow powder having the following physical properties.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe resulting oil was purified by silica gel column chromatography
  5. additionby volume mixture of benzene ethyl acetate and acetic acid

出典と根拠

ORDレコード
ord-77291116254c4c11b1dc110fd7121297
出典データセット
uspto-grants-1990_06
特許番号
US04933355

反応ノート

読み込み中…