Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod)

Norimasa Matsumoto; Ryoji Hirose; Shigeo Sasaki; Tetsuro Fujita

doi:10.1248/cpb.56.595

Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod)

Chem Pharm Bull (Tokyo). 2008 Apr;56(4):595-7. doi: 10.1248/cpb.56.595.

Authors

Norimasa Matsumoto¹, Ryoji Hirose, Shigeo Sasaki, Tetsuro Fujita

Affiliation

¹ Research Laboratory, Taito Co Ltd, Kobe, Japan.

PMID: 18379116
DOI: 10.1248/cpb.56.595

Abstract

The key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate (13), for the immunomodulatory agent FTY720 (2: fingolimod) was synthesized via Michael addition of diethyl(acetylamino)malonate (6) to 4-octanoylstyrene (12).

MeSH terms

Fingolimod Hydrochloride
Immunologic Factors / chemical synthesis*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Propylene Glycols / chemical synthesis*
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis

Substances

Immunologic Factors
Indicators and Reagents
Propylene Glycols
Fingolimod Hydrochloride
Sphingosine