BOC-D-SER-OME

colorless to light yellow liquid

Triethylamine (TEA, 183 mL, 1.3 mol) was added dropwise to a solution of compound 1_5_2 (94.0 g, 0.605 mol) in THF (3 L) at 0°C. To the resulting thick white suspension a solution of rfzTo an ice-cold solution of D-serine (5.0 g, 47.6 mmol) and NaOH (2.11 g, 52.9 mmol) in a mixture of water (110mL) and t-BuOH (110 mL) was added di-tert-butyl dicarbonate(11.38 g, 52.1 mmol) with stirring. After 1 h at 0 °C, the mixture was warmed to room temperature and stirred for 13h. The mixture was concentrated to one third its original volume using reduced pressure and water (110 mL) was added.The aqueous layer was extracted with hexanes (3 X 100 mL)and acidified to pH 1-2 by slow addition of cold 1 M KHSO4(55 mL). The resulting mixture was extracted with EtOAc (4X 150 mL). The combined organic layers were washed with water (150 mL), dried over Na2SO4, filtered and concentrated to give the crude product 3 as colorless oil (9.6 g, 98percentyield) which was used without further purification.To a white suspension of 3 (9.6 g, 46.8 mmol) and potassium carbonate (7.19 g, 52 mmol) in anhydrous DMF (50mL) was added methyl iodide (6.01 mL, 96.5 mmol). The mixture was stirred at room temperature for 1.5 h. To the resulting solution was added water (100 mL). The aqueouslayer was extracted with EtOAc (4 X 100 mL). The combined organic layers were washed with brine (2 X 175 mL), dried over Na2SO4, filtered and concentrated to give 4 as colorless oil (8.2 g, 80percent yield): []D21 +17.2 (c 5.0, MeOH), lit: []D +18.9 (c 5.0, MeOH) [15]; IR v 3388, 2978, 2936, 2886, 1740, 1691, 1456, 1437 cm-1; 1H NMR (200 MHz, acetone-d6) (ppm): 6.00 (bs, 1H, NHCO), 4.3-3.76 (m, 4H, CH2OH, OH, CHNH), 3.69 (s, 3H, OCH3), 1.41 (s, 9H, C(CH3)3); 13C NMR (50 MHz, acetone-d6) (ppm): 171.70(COOCH3), 155.89 (NHC=O), 79.05 (C(CH3)3), 62.65(CH2OH), 56.53 (CHNH), 51.84 (COOCH3), 28.08(C(CH3)3).

Protected D-Serine.

Molecular Weight:219.23
XLogP3:0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:219.11067264
Monoisotopic Mass:219.11067264
Topological Polar Surface Area:84.9
Heavy Atom Count:15
Complexity:233
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes