Réaction #172000

Équation de réaction

NH4OH

N-Boc-O-benzyl-D-serine

HOBt hydrate

EDC

→

(R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate

Rendement 87.7%

Solvants

DMF

EtOAc

Water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGIt was stirred for 18 h
2. 2
   AutreThe organic phase was separated
3. 3
   Lavagewashed with 5% NaHCO3
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of N-Boc-O-benzyl-D-serine (510 mg, 1.72 mmol) and HOBt hydrate (317 mg, 2.07 mmol) in DMF (9 mL), EDC (432 mg, 2.25 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (0.600 mL, ˜8.40 mmol) was added. It was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-tert-butyl 1-amino-3-(benzyloxy)-1-oxopropan-2-ylcarbamate (444 mg).

Source