(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 2103438Notes

Reaction equation

HRID 2103438 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0d35562aa4744b0fb74f2c4c277ccce7
Source dataset
uspto-grants-2009_08
Patent number
US07576111B2

Reaction notes

Loading…