(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → 2-((2R)-2-hydroxy-3-((4-(3-oxomorpholin-4-yl)phenyl)amino)propyl)-1H-isoindole-1,3(2H)-dione

HRID 730164

反応式

HRID 730164 の反応式
[O:1]1[CH2:3][C@@H:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C:24]2=[O:29])=[CH:19][CH:18]=1>C(O)C.O>[OH:1][C@H:2]([CH2:3][NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][C:24]2=[O:29])=[CH:21][CH:22]=1)[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

参加物

4

反応物 2

HCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimide2 回HCID 111948544-(4-Aminophenyl)morpholin-3-one

生成物 1

HCID 115167582-((2R)-2-hydroxy-3-((4-(3-oxomorpholin-4-yl)phenyl)amino)propyl)-1H-isoindole-1,3(2H)-dione

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒2 回

実験手順

A suspension of 2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione (A. Gutcait et al. Tetrahedron Asym. 1996, 7, 1641) (5.68 g, 27.9 mmol) and 4-(4-aminophenyl)-3-morpholinone (5.37 g, 27.9 mmol) in ethanol/water (9:1, 140 ml) is heated under reflux for 14 hours (the precipitate dissolves; after some time, another precipitate is formed). The precipitate (desired product) is filtered off, washed three times with diethyl ether and dried. The combined mother liquors are concentrated under reduced pressure and, after addition of a second portion of 2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3-(2H)-dione (2.84 g, 14.0 mmol), suspended in ethanol/water (9:1, 70 ml) and heated under reflux for 13 hours (the precipitate dissolves; after some time, another precipitate is formed). The precipitate (desired product) is filtered off, washed three times with diethyl ether and dried. Total yield: 10.14 g, 92% of theory.

後処理

  1. temperatureunder reflux for 14 hours (the precipitate
  2. dissolutiondissolves
  3. customafter some time, another precipitate is formed)
  4. filtrationThe precipitate (desired product) is filtered off
  5. washwashed three times with diethyl ether
  6. customdried
  7. concentrationThe combined mother liquors are concentrated under reduced pressure
  8. temperatureheated
  9. temperatureunder reflux for 13 hours (the precipitate
  10. dissolutiondissolves
  11. customafter some time, another precipitate is formed)
  12. filtrationThe precipitate (desired product) is filtered off
  13. washwashed three times with diethyl ether
  14. customdried

出典と根拠

ORDレコード
ord-cb53efc2c0044de2ace87cb64d470dd5
出典データセット
uspto-grants-2009_09
特許番号
US07582666B2

関連ノート

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