H-THR-NHME synthesis

Yield:79009-37-3 88%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol; for 16 h;

Steps:

A Synthesis of (2S,3R)-2-amino-3-hydroxy-N-methylbutanamide (Int-D):

To a solution of C (2.5 g, 9.39 mmol) in MeOH (30 mL), 10% Pd/C (50% wet, 1 g) was added and stirred under atmosphere (balloon) for 16 h. After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and washed with MeOH and 0 (250 mL, 1: 1). The filtrate was concentrated under reduced pressure to afford Int-D (1.1 g, 88%) as a white solid. H NMR (400 MHz, DMSO-d₆) δ 7.82 (br d, J = 2.5 Hz, 1H), 4.56 (br s, 1H), 3.83 - 3.75 (m, 1H), 2.88 (d, J = 4.5 Hz, 1H), 2.59 (d, J = 4.8 Hz, 3H), 2.34-1.83 (m, 2H), 1.03 (d, J = 6.4 Hz, 3H). LCMS (ESI): m/z 133.2 [M⁺+1].

References:

WO2018/26798,2018,A1 Location in patent:Page/Page column 54; 56; 57