反応 #1583892

反応方程式

DIPEA

EDC

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

HOBt

hydroxylamine hydrochloride

→

title compound

収率 6.3%

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

収率 6.3%

溶媒

EtOAc

phosphoric acid

THF

DMF

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   その他to yield a pale yellow oil
3. 3
   その他The organic layer was collected
4. 4
   洗浄washed with 1M NaOH
5. 5
   抽出extracted with EtOAc
6. 6
   その他The organic layer was evaporated
7. 7
   その他the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

実験手順

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.

出典