(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 734283

반응식

HRID 734283 반응식
[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]

참가 물질

4

반응물 2

HCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimide2회HCID 111948544-(4-Aminophenyl)morpholin-3-one

생성물 1

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

시약·촉매·용매 1

HCID 19096565Water ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a3c7e5537be435cba5763a3ee991074
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592339B2

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