2-Aminothiophenol → 3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-

HRID 1457250ノート

反応式

HRID 1457250 の反応式
COC1C=CC([C@@H]2O[C@H]2C(N)=O)=CC=1.NC1C=CC=CC=1S.N[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30][CH:31]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)[CH:32]([OH:36])[C:33]([NH2:35])=[O:34].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.ClC1C=CC=CC=1>[OH:36][C@H:32]1[C:33](=[O:34])[NH:35][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][C@H:31]1[C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1

参加物

7

反応物 4

HCID 87132-AminothiophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 10821599HCID 10821599、化合物HCID 538426453-(2-Aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

生成物 1

HCID 27336733-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, (2S,3S)-収率 82.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 7964Chlorobenzene溶媒

実験手順

A mixture of (2R,3S)-3-(4-methoxyphenyl)-2,3-epoxypropionamide (3.86 g) and chlorobenzene (77 ml) is refluxed with heating under nitrogen atmosphere. When the reflux is started, a solution of 2-aminothiophenol (2.75 g) and ferric chloride hexahydrate (0.54 mg) in methanol (0.1 ml) is added immediately into the reaction mixture, and the mixture is reacted at the same temperature for 5 minutes. The reaction mixture is subjected to HPLC analysis* to confirm the production of 3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide (6.09 g) [(2S,3S)/(2S,3R)=91.5/8.5]. To the reaction mixture is added p-toluenesulfonic acid monohydrate (0.76 g), and the mixture is refluxed for 32 hours, and concentrated under reduced pressure to remove the chlorobenzene. To the residue is added methanol (25 ml), and the mixture is refluxed for one hour, and cooled with ice overnight. The precipitated crystals are collected by filtration, washed with methanol, and dried at 50° C. to give (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (4.76 g).

後処理

  1. temperatureis refluxed
  2. temperaturewith heating under nitrogen atmosphere
  3. customthe mixture is reacted at the same temperature for 5 minutes
  4. temperaturethe mixture is refluxed for 32 hours
  5. concentrationconcentrated under reduced pressure
  6. customto remove the chlorobenzene
  7. additionTo the residue is added methanol (25 ml)
  8. temperaturethe mixture is refluxed for one hour
  9. temperaturecooled with ice overnight
  10. filtrationThe precipitated crystals are collected by filtration
  11. washwashed with methanol
  12. customdried at 50° C.

出典と根拠

ORDレコード
ord-b5c08fa0d8e84286b9c2482b456ce7f0
出典データセット
uspto-grants-1998_12
特許番号
US05847122

反応ノート

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