Reacción #496471

Ecuación de reacción

1-cyano-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

L-Alanine

→

title compound

Rendimiento 100.0%

(S)-2-[(1-Cyano-4-hydroxy-8-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid

Rendimiento 100.0%

Disolventes

sodium methoxide methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for four days before it
2. 2
   Concentraciónconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in water (20 mL)
4. 4
   Extracciónextracted with methyl t-butyl ether (2×30 mL)
5. 5
   ExtracciónThe resulting white suspension was extracted with ethyl acetate (30 mL)
6. 6
   Otrodried
7. 7
   Concentraciónconcentrated in vacuo

Procedimiento

A mixture of 1-cyano-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (101 mg, 0.31 mmol) and L-Alanine (561 mg, 6.29 mmol) in 0.5 M sodium methoxide/methanol (12 mL) was refluxed for four days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (20 mL) and extracted with methyl t-butyl ether (2×30 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (8 mL). The resulting white suspension was extracted with ethyl acetate (30 mL), dried and concentrated in vacuo to give the title compound as a white solid (117 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.52 (bs, 1H), 10.11 (br s, 1H), 8.30 (d, 1H), 8.07 (m, 1H), 7.67 (t, J=8 Hz, 1H), 7.42 (m, 2H), 7.17 (m, 3H), 4.83 (q, 1H), 1.68 (d, J=7.4 Hz); MS: (+) m/z 378.29 (M+1).

Fuente