ChemicalBook CAS DataBase List (R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid

(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid synthesis

5synthesis methods

Product Name:(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid
CAS Number:936630-57-8
Molecular formula:C10H10F3NO2
Molecular Weight:233.19

(R)-Ethyl 2,4,5-trifluoro-b-homophenylalaninateHCl

1151240-91-3
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(R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid

936630-57-8
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$75.00/1G

Yield:936630-57-8 92%

Reaction Conditions:

with hydrogenchloride in water at 27; for 6 h;Reflux;

Steps:

7 Synthesis of Compound (10) [3-Amino-4-(2,4,5-trifluorophenyl)-butyric acidj (fl-aminoacid part of Sitagliptin):
Synthesis of Compound (10) [3-Amino-4-(2,4,5-trifluorophenyl)-butyric acidj (fl-aminoacid part of Sitagliptin):2.0 M aq HC1 (15 mL) was added dropwise to 8a (3 g, 11.48 mmol) at 27°C and the resultant mixture was heated at reflux for 6 h. The reaction mixture was then allowed to cool to 27°C and concentrated in vacuo to give 10 as a colourless oil (2.46 g, 10.56 mmol, 92%). The spectralanalysis of the compound is as follows:Rf = 0.11 (Ethyl acetate); [aID25 (c 0.92, CHC13) = -6.54. ‘H NMR (300 MHz, CDC13) 67.30-7.29 (m, 1H, Aromatic), 7.11-7.08 (m, 1H, Aromatic), 4. 12-4. 10 (m, 1H, CH), 2.98-2.96 (m, 1H,CHH’), 2.88-2.84 (m, 1H, CHH’), 2.79-2.76 (m, 1H, CHH’COOH), 2.58-2.53 (m, 1H,CHH’COOH), 2.03 (brs, 2H, NH2) ppm ‘3C NMR (75 MHz, CDC13) 6 177.4, 159.8, 152.6,146.8, 123.2, 122.8, 120.4, 118.5, 105.6, 49.2, 45.6, 34.2 ppmJR (CHC13) v 2935, 1720 cm’ ESJMS: m/z (%) 233 [Mj. Analysis calculated for C,H,F3NO2 C 51.51, H 4.32, N 6.01. Found C 51.50, H 4.28, N 5.96.

References:

COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH;BARUA, Nabin Chandra;SAIKIA, Bishwajit;BORAH, Preetismita;BAISHYA, Gakul WO2015/189862, 2015, A1 Location in patent:Page/Page column 26; 27

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