反応 #1076700

反応方程式

t-butyloxycarbonyl-O-benzyl-D-serine

sodium bicarbonate

methyl iodide

→

desired compound

収率 96.0%

tert-Butyloxycarbonyl-O-benzyl-D-serine methyl ester

収率 96.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   濃縮the reaction mixture was concentrated to approximately 100 mL
2. 2
   workup.ADDITIONEthyl acetate was added
3. 3
   洗浄the mixture washed with aqueous sodium bicarbonate and brine
4. 4
   抽出The organic extract
5. 5
   その他was dried
6. 6
   濃縮concentrated

実験手順

To a solution of t-butyloxycarbonyl-O-benzyl-D-serine (25.0 g, 84.7 mmol) stirring in dimethylformamide (500 mL) at room temperature was added sodium bicarbonate (14.2 g, 169 mmol) followed by methyl iodide (26.4 mL, 424 mmol). After 18 h, the reaction mixture was concentrated to approximately 100 mL. Ethyl acetate was added and the mixture washed with aqueous sodium bicarbonate and brine. The organic extract was dried and concentrated to give the desired compound (25 g, 96%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) d 1.45 (s, 9H), 3.70 (m, 1H), 3.75 (s, 3H), 3.85 (m, 1H), 4.50 (m, 3H), 7.30 (m, 5H); MS (FD) m/e 310; Anal. calc'd for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.31; H, 7.49; N, 4.43.

出典