反応 #1994331

反応方程式

N-(tert-butoxycarbonyl)-D-alanine

benzyl [(1S)-2-amino-1-benzylethyl]carbamate

HBTU

triethylamine

→

title compound

収率 99.0%

Benzyl [(1S)-1-benzyl-2-({(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl}amino)ethyl]carbamate

収率 99.0%

溶媒

water

DMF

反応条件

後処理

1. 1
   抽出The mixture was extracted with ethyl acetate/heptane 5/1 (2×20 mL)
2. 2
   洗浄the combined extracts were washed with 1N citric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL)
3. 3
   乾燥The organic layer was dried over sodium sulfate
4. 4
   濃縮concentrated under reduced pressure

実験手順

To a solution of N-(tert-butoxycarbonyl)-D-alanine (595 mg, 3.14 mmol) in DMF (20 mL) was added benzyl [(1S)-2-amino-1-benzylethyl]carbamate (Tet. Lett. 2005, 46(41), 7069) (968 mg, 3.30 mmol), HBTU (1.43 g, 3.77 mmol) and triethylamine (1.8 ml, 12.6 mmol) at room temperature. After stirring the reaction mixture for 15 hours, water (20 mL) was added to the mixture. The mixture was extracted with ethyl acetate/heptane 5/1 (2×20 mL) and the combined extracts were washed with 1N citric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound as a white solid in 99% yield, 1.42 g. 1H NMR (400 MHz, CDCl3) : 1.24 (d, 3H), 1.43 (s, 9H), 2.59-2.86 (m, 4H), 3.13-3.25 (m, 2H), 3.34-3.44 (m, 1H), 3.89-4.05 (m, 2H), 4.90-5.05 (m, 2H), 7.11-7.36 (m, 10H).

出典