BOC-D-2,4,5-TRIFLUOROPHE

White powder

4.5 A solution of 2.41 g (7.5 rnmol) of (/?)-//-(tert-butoxycarbonyl)-2, 4, 5-trifluorophenylalanine methyl ester in approximately 200 mL of a mixture oftetrahydrofuran:methanol: IN lithium hydroxide (3:1:1) was stirred at 50 C for 4 h. The reaction wascooled, acidified with 5% hydrochloric acid (aqueous) and extracted with ethyl acetate. The combinedorganic phases were washed with brine, dried over magnesium sulfate and concentrated in vacuo to givethe title compound. LC-MS 220.9 (M+l - BOC).4.6 (R)-3-(tert-Butoxycarbonylamino)-4-(2, 4, 5-trifluorophenyl)butanoic acid 7 To a solution of To a solution of 0.37 g (1.16 mmol) of [(R)-N-(L, L-DIMETHYLETHOXY-] [CARBONYL) -2, 4, 5-TRIFLUOROPHENYLALANINE IN 10 ML OF DIETHYL ETHER AT-20 C WERE ADDED] sequentially 0.193 mL (1.3 mmol) of triethylamine and 0.18 mL (1.3 mmol) of isobutyl chloroformate, and the reaction was stirred at this temperature for 15 min. A cooled ethereal solution of diazomethane was then added until the yellow color persisted and stirring was continued for a further 1 h. The excess diazomethane was quenched by dropwise addition of acetic acid, and the reaction was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography (silica gel, 3: 1 hexane: ethyl acetate) afforded 0.36 g of diazoketone. To a solution of 0.35 g (1.15 mmol) of the diazoketone dissolved in 12 mL of 1, 4-dioxane : water (5: 1) was added 26 mg (0.113 mmol) of silver benzoate. The resultant solution was sonicated for 2 h before diluting with ethyl acetate and washing sequentially with IN hydrochloric acid and brine, drying over magnesium sulfate and concentrating in vacuo. Purification by flash chromatography (silica gel, 97: 2: 1 dichloromethane: methanol: acetic acid) afforded 401 mg of the title compound. 1H NMR (500 MHz, [CDC13)] [8] 7.06 (m, 1H), 6.95 (m, 1H), 5.06 (bs, 1H), 4.18 (m, [1H), ] 2.98 (m, 2H), 2.61 (m, 2H), 1.39 (s, 9H).Step D. (3R)-3-r (1, 1-Dimethyletycarbonyl) aminol-4(2, 4, 5- trifluorophenyl)-butanoic acid; To a solution of 0.37 g (1.16 mmol) of (R)-N-(l, l- dimethylethoxycarbonyl) -2, 4, 5-trifluorophenylalanine in 10 mL of diethyl ether at-20 C were added sequentially 0.193 mL (1.3 mmol) of triethylamine and 0.18 mL (1.3 mmol) of isobutyl chloroformate, and the reaction was stirred at this temperature for 15 min. A cooled ethereal solution of diazomethane was then added until the yellow color persisted and stirring was continued for a further 1 h. The excess diazomethane was quenched by dropwise addition of acetic acid, and the reaction was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography (silica gel, 3: 1 hexane: ethyl acetate) afforded 0.36 g of diazoketone. To a solution of 0.35 g (1.15 mmol) of the diazoketone dissolved in 12 mL of 1, 4-dioxane : water (5: 1) was added 26 mg (0.113 mmol) of silver benzoate. The resultant solution was sonicated for 2 h before diluting with ethyl acetate and washing sequentially with 1N hydrochloric acid and brine, drying over magnesium sulfate and concentrating in vacuo. Purification by flash chromatography (silica gel, 97: 2: 1 dichloromethane: methanol: acetic acid) afforded 401 mg of the title compound. 1H NMR (500 MHz, CDC13) 6 7.06 (m, 1H), 6.95 (m, 1H), 5.06 (bs, 1H), 4.18 (m, 1H), 2.98 (m, 2H), 2.61 (m, 2H), 1.39 (s, 9H).To a solution of 0.37 g (1.16 mmol) of (R)-N-(TERT-BUTOXYCARBONYL)-2, 4, 5- trifluorophenylalanine in 10 ML of diethyl ether at-20 C were added sequentially 0.193 mL (1.3 mmol) of triethylamine and 0.18 mL (1.3 mmol) of isobutyl CHLOROFORMATE, and the reaction was stirred at this temperature for 15 min. A cooled ethereal solution of diazomethane was then added until the yellow color persisted and stirring was continued for a further 1 h. The excess diazomethane was quenched by dropwise addition of acetic acid, and the reaction was diluted with ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. Purification by flash chromatography (silica gel, 3: 1 hexane: ethyl acetate) afforded 0.36 g of diazoketone. To a solution of 0.35 g (1.15 mmol) of the diazoketone dissolved in 12 mL of 1, 4-dioxane : water (5: 1) was added 26 mg (0.113 mmol) of silver benzoate. The resultant solution was sonicated for 2 h before diluting with ethyl acetate and washing sequentially with 1N hydrochloric acid and brine, drying over magnesium sulfate and concentrating in vacuo. Purification by flash chromatography (silica gel, 97: 2: 1 dichloromethane: methanol: acetic acid) afforded the title compound. 1H NMR (500 MHz, CDC13) : 8 7.06 (m, 1H), 6.95 (m, 1H), 5.06 (bs, 1H), 4.18 (m, 1H), 2.98 (m, 2H), 2.61 (m, 2H), 1.39 (s, 9H).

Molecular Weight:319.28
XLogP3:2.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:6
Exact Mass:319.10314248
Monoisotopic Mass:319.10314248
Topological Polar Surface Area:75.6
Heavy Atom Count:22
Complexity:413
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes