(S)-(+)-N-(2,3-Epoxypropyl)phthalimide → (S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one

HRID 1796942Notes

Reaction equation

HRID 1796942 reaction equation
O1C[C@@H]1C[N:5]1C(=O)C2[C:7](=[CH:8]C=CC=2)[C:6]1=O.[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.[CH2:30]([OH:32])C.[OH2:33]>>[NH2:5][CH2:6][C@@H:7]1[O:33][C:30](=[O:32])[N:16]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[CH:21][CH:22]=2)[CH2:8]1

Participants

4

Reactant 3

HCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimide2×HCID 111948544-(4-Aminophenyl)morpholin-3-oneHCID 19096565Water ethanol2×

Product 1

HCID 11346837(S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one

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 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.

Workup

  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

Sources & evidence

ORD record
ord-c634bc47928c40cdac410278626ce62b
Source dataset
uspto-grants-2006_04
Patent number
US07034017B2

Reaction notes

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