1-Phenethylamine → (R)-N2-[(1,1-Dimethylethoxy)carbonyl]-N-(1-methyl-2-phenylethyl)-L-allothreoninamide

To a solution of N-Boc-L-allothreonine (0.325 g, 1.48 mmol, 1.00 eq.) and 1-hydroxybenzotriazole hydrate (0.221 g, 1.64 mmol, 1.11 eq.) in dimethylformamide (5 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (WSC) (0.312 g, 1.63 mmol, 1.10 eq.). After 0.5 hr, a solution of (R) α-methylbenzylamine (0.20 mL, 1.55 mmol, 1.05 eq.) in dimethylformamide (3 mL) was added, followed by 4-methylmorpholine (0.16 mL, 1.46 mmol, 0.98 eq.). After 17 hr, the reaction mixture was poured into a brine/water solution (1:1) and extracted twice with ethyl acetate. The organic layers were combined and washed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate, water, dried over sodium sulfate, and the organic layer concentrated in vacuo to give title compound (0.448 g, 93.9%):

1. waitAfter 17 hr
2. extractionextracted twice with ethyl acetate
3. washwashed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate, water
4. dry with materialdried over sodium sulfate
5. concentrationthe organic layer concentrated in vacuo

ORD record

ord-2e881179245d4df1b236c32befc74f36

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05561146