O-Xylene → HCID 10829366、化合物

HRID 1418721ノート

反応式

HRID 1418721 の反応式
C1(C)C(C)=CC=CC=1.NC1C=CC=CC=1S.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24][CH:25]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[CH:26]([OH:30])[C:27]([NH2:29])=[O:28]>CO.C(O)C.O>[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24][C@@H:25]([C:31]1[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=1)[C@@H:26]([OH:30])[C:27]([NH2:29])=[O:28]

参加物

7

反応物 3

HCID 7237O-XyleneHCID 87132-AminothiophenolHCID 538426453-(2-Aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

生成物 1

HCID 10829366HCID 10829366、化合物収率 31.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of (2R,3S)-3-(4-methoxyphenyl)glycidamide (1.93 g) and xylene (15 ml) is refluxed under nitrogen atmosphere. To the reaction solution is added a solution of 2-aminothiophenol (1.38 g) and iron sulfate·heptahydrate (0.28 mg) in methanol (0.2 ml) immediately after the refluxing starts. After reaction at the same temperature for 5 minutes, the reaction solution is cooled to room temperature. The reaction solution is subjected to HPLC analysis to confirm the production of 3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide (2.69 g) (threo/erythro=91/9). The reaction solution is concentrated under reduced pressure to remove the solvent, and the residue thus obtained is dissolved with heating in ethanol (3 ml) and water (3 ml). The solution is gradually cooled with stirring to 0° C. for crystallization. The precipitated crystals are collected by filtration. The collected crystals are washed with iced 50% ethanol, and dried at 50° C. to give (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propioamide (0.84 g).

後処理

  1. temperatureis refluxed under nitrogen atmosphere
  2. customAfter reaction at the same temperature for 5 minutes
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. customto remove the solvent
  5. customthe residue thus obtained
  6. dissolutionis dissolved
  7. temperatureThe solution is gradually cooled
  8. filtrationThe precipitated crystals are collected by filtration
  9. washThe collected crystals are washed with iced 50% ethanol
  10. customdried at 50° C.

出典と根拠

ORDレコード
ord-d1777c7da8a54aa99d02f71951b7223d
出典データセット
uspto-grants-1999_03
特許番号
US05883264

反応ノート

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