ChemicalBook CAS DataBase List Gilenia

Gilenia synthesis

9synthesis methods

Product Name:Gilenia
CAS Number:162359-55-9
Molecular formula:C19H33NO2
Molecular Weight:307.47

Fingolimod is used to treat multiple sclerosis, and has antineoplastic activity.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

Shaikh, Rizwan S.; Schilson, Stefanie S.; Wagner, Stefan; Hermann, Sven; Keul, Petra; Levkau, Bodo; Schaefers, Michael; Haufe, Guenter. Synthesis and Evaluation of Fluorinated Fingolimod (FTY720) Analogues for Sphingosine-1-Phosphate Receptor Molecular Imaging by Positron Emission Tomography. Journal of Medicinal Chemistry. Volume 58. Issue 8. Pages 3471-3484. Journal; Online Computer File. (2015).

N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide

249289-10-9
100 suppliers
$105.00/50mg

162359-55-9
196 suppliers
$7.00/5mg

Yield:162359-55-9 82%

Reaction Conditions:

with sodium hydroxide in methanol for 5 h;Reflux;

Steps:

12.5 12.5 2-Amino-2-(4-octylphenethyl)propane-1 ,3-diol (FTY 720) (SSS 798)
Protected aminodiol 71 (349 mg, 1.0 mmol) was dissolved in methanol (20 mL) and treated with 1 M sodium hydroxide solution (1.2 mL, 1.2 mmol, 1.2 eq.). The reaction mixture was heated to reflux for 5 h. After cooling to r.t. the mixture was diluted with 1 M sodium hydroxide solution (15 mL) and the aqueous phase was extracted with dichloromethane (5 x 20 mL). The combined organic layers were dried over Na₂S0₄ and concentrated in vacuo. The product was crystallized from ethyl acetate to give a white solid. Yield: 252 mg (82%). 72 M.p.: 127 °C (lit. 121 -124 °C) ¹H-NMR (300 MHz, CD₃OD, CDCI₃) δ [ppm]: 0.87 (m, 3 H, 19-CH₃), 1 .22-1.37 (m, 10 H, 14-CH₂ to I 8-CH₂), 1 .57 (m, 2 H, 13-CH₂), 1 .69 (m, 2 H, 4-CH₂), 2.51 -2.65 (m, 4 H, 5-CH₂, 12-CHz), 3.48 (d, ²JH,H = 10.9 Hz, 2 H, 1 -CH₂, 3-CH₂), 3.54 (d, ²J_H,H = 1 1.0 Hz, 2 H, 1 -CH₂, 3-CHz), 7.09 (m, 4 H, 7-CH, 8-CH, 10-CH, 1 1 -CH). ¹³C-NMR (75 MHz, CD₃OD, CDCI₃) δ [ppm]: 14.3 (q, C-19), 23.2 (t, C-18), 29.5, 29.9, 30.1 (t, C-13 to C-16), 32.2 (t, C-5), 32.5 (t, C-4), 36.1 (t, C-17), 37.0 (t, C-12), 56.4 (s, C-2), 66.2 (t, C-1 , C-3), 128.7, 129.0 (d, C-7, C-8, C-10, C-1 1 ), 140.1 , 140.9 (s, C-6, C-9). Exact mass (ESI⁺): C19H33NO2 + H⁺: calcd. 308.2584, found 308.2585; C19H33NO2 + Na⁺: calcd. 330.2404, found 330.2408; + Na⁺: calcd. 637.4915, found 637.4917. Ref.: Spectroscopic data agree with those given in S. Kim, H. Lee, M. Lee, T. Lee, Synthesis 2006, 5, 753-755.

References:

WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER;HAUFE, Guenter;LEVKAU, Bodo;SCHAEFERS, Michael;SCHILSON, Stefani Silke;KEUL, Petra WO2013/26765, 2013, A1 Location in patent:Page/Page column 66-67

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