(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

Reaktionsgleichung

Reaktionsgleichung von HRID 68468
[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 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7fb07ecdb1c478cb22023cf93ed5e08
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822458B2

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