Hydrochloric Acid → N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine

HRID 465916

反応式

HRID 465916 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:13](Cl)(=[O:17])[O:14][CH2:15][CH3:16].[NH2:19][CH2:20][CH2:21][SH:22].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:15]([O:14][C:13]([O:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:19][CH2:20][CH2:21][SH:22])=[O:9])=[O:17])[CH3:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 10928Ethyl chloroformateHCID 752314-Methoxysalicylic Acid

生成物 1

HCID 14719509N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine収率 89%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

反応条件

温度
-15 °C

実験手順

Under argon atmosphere, 2.84 g of 4-methoxysalicylic acid was dispersed in 45 ml of methylene chloride, and the dispersion was cooled to -15° C. To the dispersion was added 3.76 g of triethylamine and 3.77 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hour. To the mixture was added a solution of 1.56 g of cysteamine in 5 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 4.50 g of N-(2-ethoxycarbonyloxy-4-methoxybenzoyl)cysteamine.

後処理

  1. stirringthe mixture was agitated at -15° C. for 2 hours
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off in evacuated atomosphere

出典と根拠

ORDレコード
ord-3ae318039fa6472396b71c8f4c0654bb
出典データセット
uspto-grants-1992_10
特許番号
US05155106

関連ノート

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