L-Serine,N-[(1,1-dimethylethoxy)carbonyl]-, hydrazide synthesis

Yield:2766-42-9 93.7%

Reaction Conditions:

with hydrazine hydrate in methanol at 50;

Steps:

1 Synthesis of tert-butyl (S)-(l-hydrazineyl-3-hydroxy-l-oxopropan-2-yl)carbamate

To L-Boc-Ser-OMe (25 g, 114 mmol) in methanol (100 mL) was added hydrazine hydrate (25 mL, 402 mmol). The solution was stirred at 50 ^°C overnight. The following day the solvent was removed under reduced pressure and the resulting solid dried under hi-vac to a constant weight to give tert-butyl (S)-(l-hydrazineyl-3-hydroxy-l-oxopropan-2-yl)carbamate (23.4 g, 93.7%). NMR DMSO 9.0 (s, 1H), 6.5 (d, 1 H), 4.8 (s, 1H), 4.2 (s, 2H), 3.9 (m, 1 H), 3.5 (s, 2 H), 1.4 (s, 9H).

References:

WO2020/18929,2020,A1 Location in patent:Page/Page column 21