H-THR(TBU)-OME HCL

White to off white powder

HATU (0.585 g, 1.54 mmol) was added to a solution of 3'-Fluoro-4'-(methyloxy)-3- nitro-4-biphenylcarboxylic acid (0.300 g, 1.03 mmol), methyl O-(1 , 1-dimethylethyl)- L-threoninate hydrochloride (0.232 g, 1.03 mmol), and diisopropylethylamine (0.27 mL, 1.54 mmol) in 10 mL of DMF. The mixture was stirred at room temperature overnight, and then diluted with ethyl acetate, and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. Chromatography on silica gel with hexane/ethyl acetate gave 0.392 g (82% yield) g of desired product as a white solid.To a stirred solution of O-fe/f-butyl L-Threonine methyl ester hydrochloride (2.0 g. 8.86 mmol, 1 eq) and phenyl dichlorophosphate (1 .32 ml, 8.86 mmol, 1 eq) in anhydrous CH2CI2 ( 00 ml) was added dropwise at -78 C anhydrous Et3N (2.41 ml, 17.72 mmol, 2 eq). Following the addition, the reaction mixture was stirred at -78 C for 30 min and then at room temperature for 1 h. Formation of the desired compound was monitored by 31 PNMR. After this period the solvent was removed under reduced pressure to give an oil. The product was then purified by flash column chromatography (eluting with hexane - ethyl acetate 70:30 v/v) giving the desired compound in 96% yield (3.10 g). (0247) C15H23CINO5P; M.W: 363.77; 1 H NMR (CDCI3, 500 MHz) delta 7.40 - 7.35 (m, 2H, Ph), 7.31 - 7.26 (m, 2H, Ph), 7.26 - 7.21 (m, 1 H, Ph), 4.45 (m, 1 H, NH), 4.20 (m, 1 H, CH3CH), 3.97 (m, 1 H, CHNH), 3.76 (s, 1 .5H, OCH3), 3.74 (s, 1 .5H, OCH3), 1 .29 (d, J = 6.2 Hz, 1 .5H, CH3), 1 .27 (d, J = 6.2 Hz, 1 .5H, CH3), 1 .12 (s, 9H, C(CH3)3); 31 P NMR (CDCI3, 202 MHz) delta 9.71 , 8.98.

Molecular Weight:225.71
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:225.1131712
Monoisotopic Mass:225.1131712
Topological Polar Surface Area:61.6
Heavy Atom Count:14
Complexity:174
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes