Reaction #172000

Reaction equation

NH4OH

N-Boc-O-benzyl-D-serine

HOBt hydrate

EDC

→

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

Yield 87.7%

Solvents

DMF

EtOAc

Water

Conditions

Workup

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

Procedure

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