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ChemicalBook CAS DataBase List N-[4-(AMinocarbonyl)-3-fluorophenyl]-2-Methylalanine
1242137-20-7

N-[4-(AMinocarbonyl)-3-fluorophenyl]-2-Methylalanine synthesis

1synthesis methods
-

Yield:-

Reaction Conditions:

with potassium carbonate;copper(l) iodide;2-acetylcyclohexanone;triethylamine in water;N,N-dimethyl-formamide at 95 - 100; for 48 h;

Steps:

6b

4-Bromo-2-fluorobenzamide (0.5 g, 2.29 mmol), 2 aminoisobutyric acid (0.354 g,3.54 mmol), CuI (87 mg, 0.458 mmol), and K2CO3 (0.790 g, 5.72 mmol) were mixed in DMF (5 mL). H2O (0.5 mL) and TEA (11 mg, 0.1 mmol) were added followed by 2-acetyl cyclohexanone (60 mg, 0.428 mmol). The reaction mixture was heated to 95-100 °C for 48 h. The reaction mixture was diluted with H2O (20 mL) and the aqueous layer was washed with ethyl acetate (20 mL). The aqueous layer was acidified with IM citric acid to pH 4 and the product was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the product. 1H NMR (DMSO, Freebase): δ (ppm) 7.55-7.45 (t, IH), 7.20 (bs, IH), 7.05 (bs, IH), 6.80 (bs, IH), 6.35-6.30 (d, IH), 6.18-6.10 (d, IH), 1.42 (s, 6H).

References:

WO2010/99238,2010,A1 Location in patent:Page/Page column 33

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