反应 #1884972

反应方程式

1(R)-tert-butoxycarbonylamino-2(S)-vinyl-cyclopropanecarboxylic acid ethyl ester

LiOH

→

title compound

收率 87.3%

1(R)-tert-butoxycarbonylamino-2(S)-vinyl-cyclopropanecarboxylic acid

收率 87.3%

溶剂

THF

methanol

water

反应条件

后处理

1. 1
   其他quenched with 1N NaOH (15 mL) and water (20 mL)
2. 2
   洗涤The resulting mixture was washed with ethyl acetate (20 mL)
3. 3
   萃取the organic phase was extracted with 20 mL 0.5N NaOH
4. 4
   萃取extracted with ethyl acetate (3×40 mL)
5. 5
   洗涤The combined organic extracts were washed with brine
6. 6
   干燥dried (MgSO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated

实验过程

To a solution of 1(R)-tert-butoxycarbonylamino-2(S)-vinyl-cyclopropanecarboxylic acid ethyl ester (3.28 g, 13.2 mmol) in THF (7 mL) and methanol (7 mL) was added a suspension of LiOH (1.27 g, 53.0 mmol) in water (14 mL). The mixture was stirred overnight at room temperature and quenched with 1N NaOH (15 mL) and water (20 mL). The resulting mixture was washed with ethyl acetate (20 mL), and the organic phase was extracted with 20 mL 0.5N NaOH. The combined aqueous phases were acidified with 1N HCl until pH 4 and extracted with ethyl acetate (3×40 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to yield the title compound as a white solid (2.62 g, 87%). 1H NMR: (DMSO-d6) 1.22-1.26 (m, 1H), 1.37 (s, 9H), 1.50-1.52 (m, 1H), 2.05 (q, J=9 Hz, 1H), 5.04 (d, J=10 Hz, 1H), 5.22 (d, J=17 Hz, 1H), 5.64-5.71 (m, 1H), 7.18, 7.53 (s, NH (rotamers), 12.4 (br s, 1H)); MS m/z 228 (M++H).

来源