METHYL 2-(4-((TERT-BUTOXYCARBONYL)AMINO)PHENOXY)ACETATE synthesis

Yield:632388-02-4 70%

Reaction Conditions:

with caesium carbonate;potassium iodide in acetone; for 4 h;Heating / reflux;

Steps:

1.a Step a: Methyl (4-tert-butoxycarbonylaminophenoxy)acetate.

tert-Butyl (4-hydroxyphenyl) carbamate (prepared by the method J. Med. Chem., 1995, 38, (20), pp. 3983-3994), (13.12 g, 62.7 MMOL) is dissolved in 150 ML of acetone, followed by addition of caesium carbonate (1.1 eq, 69 mmol ; 22.5 g) and one crystal of potassium iodide. The reaction medium is REFLUXED for four hours. The crude product is filtered off and then evaporated to dryness. The residue is taken up in ethyl acetate and washed with saturated bicarbonate solution. The organic phase is dried over NA2SO4 and then evaporated to dryness. The product is obtained is chromatographed on silica with 4: 1 hexane/EtOAc (Rf = 0.25) to give 12.3 [G] of the expected compound. YIELD = 70% 1H NMR (CDCI3) : 1.49 (9H, s); 3.79 (3H, s); 4.59 (2H, s); 6.34 (1H, broad s); 6.79-6. 89 (2H, m); 7.15-7. 32 (9H, s)

References:

WO2003/103567,2003,A2 Location in patent:Page 33