(S)-(+)-Glycidyl Phthalimide

Chemical Properties

White powder

Uses

(S)-(+)-Glycidyl Phthalimide is a phthalimide derivative used as an intermediate in the preparation of the antibiotic Linezolid (L466500). It is also a key intermediate of rivaroxaban.

Application

(S)-(+)-glycidyl phthalimide is primarily used as a key chiral intermediate in the synthesis of rivaroxaban, a structural unit for linezolid and antifungal thiazolidinones/oxazolidinones, a reference standard for rivaroxaban impurity 92 in quality control, and a chiral source for the synthesis of complex organic molecules with chiral hydroxyl/amino groups.

Synthesis

Phthalimide and (S)-1-substituent propylene oxide are used as raw materials, a reaction occurs under the action of a catalyst to generate 2-((S)-3-substituent-2-hydroxypropyl isodihydroindole-1,3-dione, and finally (S)-glycidyl phthalimide is generated by means of a ring-closure reaction.

References

[1] Patent: WO2004/112787, 2004, A1. Location in patent: Page 17-18
[2] Patent: WO2004/113301, 2004, A1. Location in patent: Page 18
[3] Tetrahedron Asymmetry, 1996, vol. 7, # 6, p. 1641 - 1648
[4] Heterocycles, 2006, vol. 67, # 2, p. 561 - 566
[5] Chemical communications (Cambridge, England), 2003, # 4, p. 468 - 469