(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

Reaktionsgleichung

Reaktionsgleichung von HRID 730164
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cb53efc2c0044de2ace87cb64d470dd5
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582666B2

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