(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 68468

反応式

HRID 68468 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 refluxed for 14 h (the precipitate dissolves, after some time again formation of a precipitate). 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 refluxed for 13 h (the precipitate dissolves, after some time again formation of a precipitate). 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. dissolutiondissolves
  2. filtrationThe precipitate (desired product) is filtered off
  3. washwashed three times with diethyl ether
  4. customdried
  5. concentrationThe combined mother liquors are concentrated under reduced pressure
  6. temperaturerefluxed for 13 h (the precipitate
  7. dissolutiondissolves
  8. filtrationThe precipitate (desired product) is filtered off
  9. washwashed three times with diethyl ether
  10. customdried

出典と根拠

ORDレコード
ord-d7fb07ecdb1c478cb22023cf93ed5e08
出典データセット
uspto-grants-2014_09
特許番号
US08822458B2

関連ノート

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