Reaktion #496471

Reaktionsgleichung

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

L-Alanine

→

title compound

Ausbeute 100.0%

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

Ausbeute 100.0%

Lösungsmittel

sodium methoxide methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle