Reaktion #496472

Reaktionsgleichung

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

D-Alanine

sodium methoxide methanol

→

title compound

Ausbeute 79.5%

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

Ausbeute 79.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for three days before it
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in water (25 mL)
4. 4
   Extraktionextracted with dichloromethane (3×30 mL)
5. 5
   ExtraktionThe white suspension was extracted with ethyl acetate (30 mL) and dichloromethane (30 mL)
6. 6
   WaschenThe combined organic layers were washed with brine
7. 7
   Trocknendried over MgSO4
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 1-cyano-4-hydroxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (95 mg, 0.30 mmole), D-Alanine (529 mg, 5.94 mmole) and 0.5 M sodium methoxide/methanol (11.3 mL) was refluxed for three days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (25 mL) and extracted with dichloromethane (3×30 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (8 mL). The white suspension was extracted with ethyl acetate (30 mL) and dichloromethane (30 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound as a white solid (90 mg): 1H NMR (DMSO-d6, 200 MHz): δ=13.52 (bs, 1H), 9.15 (br s, 1H), 8.30 (d, 1H), 8.10 (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=7.0 Hz, 3H)); MS: (+) m/z 378.29 (M+1).

Quelle