BOC-D-TYR-OME

White to off-white powder

Potassium carbonate (250.9g, 1.815mol) was added to 1.0L of water, stir, under ice-water bath was added compound 11 (140.2g, 0.605mol), and then added dropwise Boc2O in 0 ~ 10 (158.4g, 0.726mol) in ethanol (300mL) was added. After the dropwise addition the reaction to naturally warm to room temperature 2h, TLC monitored the reaction was complete. With ethyl acetate (600mLX3) extracted, and the combined organic phase was washed with 1N hydrochloric acid (400mL) washed with, water (400mL) washed with saturated brine (400mLX2), dried over anhydrous sodium sulfate. Filtered, and the filtrate was concentrated under reduced pressure to give a solid, it is washed with 300mL of hexane, and drying, 175.8 g white solid, yield 98.4percentS) -1- ( (tert-butoxycarbonyl) amino) -2- (4-hydroxyphenyl) ethyl acetate To a solution of 120.0 g of the product of Step 1(0.518 mol, 1.0 eq) in 600 mL DCM wasadded 104.8 g TEA (1.04 mol, 2.0 eq) at 0 5°C. After stirred below 5°C for 30 minutes, 124.3 gBoc2O (0.570 mol, 1.1 eq) was added portion-wise. The resulting solution was stirred at 25 °C for18 hrs, and TLC (PE/EA = 2/1) showed the reaction was finished. The solution was diluted with200 mL DCM and washed with 1 M citric acid aqueous solution (400 mLx 1, 300 mLx 1), water(300 mLx 1) and brine (300 mLx 1), dried over anhydrous Na2 SO4 and concentrated to give crudeproduct, which was crystallized from (DCMIPE = 100 mL/700mL) to afford 128.5 g of the titlecompound, 2-step yield: 82.8percent.A mixture of (R)-methyl 2-amino-3-(4-hydroxyphenyl)propanoate (2.28 g, 11.68 mmol), sodium bicarbonate (2.8 g, 33.3 mmol), and di-tert-b tyl dicarbonate (2.8 g, 12.83 mmol) in 50 mL EtOH was stirred at room temperature overnight. The resulting mixture was partitioned between EtOAc and water. The aqueous phase was removed. The organic phase was dried over MgS0To a 3 L round bottom flask was added crude (R)-methyl 2-amino-3-(4-hydroxyphenyl)propanoate (202 g, 871.8 mmol, 1.00 eq), triethylamine (221 g, 2.2 mol, 2.50 eq) and DCM (1 L) to give a slurry. The slurry was cooled in an ice bath and asolution of (Boc)20 (209 g, 959 mmol, 1.10 eq) in DCM (1 L) was added drop-wise.After the addition, the resulting colorless solution was warmed to 10 °C and stirred for18 hrs. To the mixture was added water (1.5 L), followed by the slow addition ofconcentrated HCI until pH 3 was achieved. The organic phase was separated, washed with diluted HCI (0.2 mol/L, 1.5 L) and brine (1.5 L x2). The organic phase was dried over anhydrous Na2504, filtered and concentrated under reduced pressure to provide crude product. To the crude product was added DCM (400 ml) and PE (2 L) to give a white suspension. The suspension was stirred at 10 °C for 1 h then filtered. Theresulting filter cake was dried under vacuum to provide 210 g of the title compound as a solid, which was taken to the next step without any further purification.

Molecular Weight:295.33
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:295.14197277
Monoisotopic Mass:295.14197277
Topological Polar Surface Area:84.9
Heavy Atom Count:21
Complexity:356
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes