Reaction #1583892

Reaction equation

DIPEA

EDC

(R)-3-t-butoxycarbonylamino-4-phenylbutyric acid

HOBt

hydroxylamine hydrochloride

→

title compound

Yield 6.3%

((R)-1-Benzyl-2-hydroxycarbamoylethyl)carbamic Acid t-Butyl Ester

Yield 6.3%

Solvents

EtOAc

phosphoric acid

THF

DMF

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   Otherto yield a pale yellow oil
3. 3
   OtherThe organic layer was collected
4. 4
   Washwashed with 1M NaOH
5. 5
   Extractionextracted with EtOAc
6. 6
   OtherThe organic layer was evaporated
7. 7
   Otherthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Procedure

DIPEA (32.7 mL, 188 mmol) and EDC (15.4 g, 80.5 mmol) were added to a solution of (R)-3-t-butoxycarbonylamino-4-phenylbutyric acid (15.0 g, 53.7 mmol), HOBt (7.3 g, 53.7 mmol), and hydroxylamine hydrochloride (7.5 g, 107 mmol) in DMF (150 mL). The mixture was stirred at room temperature for 1 day and then concentrated in vacuo to yield a pale yellow oil. The oil was distributed between 5% THF in EtOAc and 1M phosphoric acid. The organic layer was collected and washed with 1M NaOH. The alkaline aqueous layer was then acidified using 1M phosphoric acid and extracted with EtOAc. The organic layer was evaporated and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to afford the title compound as a white solid (1.0 g, 3.4 mmol). MS m/z: [M+H+] calcd for C15H22N2O4, 295.16. found 295.2.

Source