Reacción #632016

Ecuación de reacción

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

LiOH

→

desired compound

Rendimiento 87.3%

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

Rendimiento 87.3%

Disolventes

THF

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with 1N NaOH (15 mL) and water (20 mL)
2. 2
   LavadoThe resulting mixture was washed with ethyl acetate (20 mL)
3. 3
   Extracciónthe organic phase was extracted with 20 mL 0.5N NaOH
4. 4
   Extracciónextracted with ethyl acetate (3×40 mL)
5. 5
   LavadoThe combined organic extracts were washed with brine
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

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 to pH 4 and extracted with ethyl acetate (3×40 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to provide the desired compound as a white solid (2.62 g, 87%). 1HNMR: (DMSO-d6) δ 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)); LC-MS (retention time: 1.67 minutes, method B), MS m/z 228 (M++H).

Fuente