Reaktion #337543

Reaktionsgleichung

MeONa

MeOH

4-Hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester

(S)-alanine

→

title compound

Ausbeute 59.0%

2-(S)-[(4-Hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid

Ausbeute 59.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated in vacuo
2. 2
   workup.ADDITIONTo the residue was added water (15 ml)
3. 3
   Waschenthe mixture was washed with Et2O (3×30 ml)
4. 4
   SonstigeThe so purified aq. solution
5. 5
   workup.ADDITIONwas acidified by the addition of 6 N HCl
6. 6
   Extraktionextracted with EtOAc (1×30 ml)
7. 7
   TrocknenThe organic phase was dried over MgSO4
8. 8
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 4-Hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester (176 mg, 0.5 mmol), (S)-alanine (225 mg, 2.5 mmol) and a 0.5 N solution of MeONa in MeOH (5 ml, 2.5 mmol) was heated in a microwave oven with stirring for 20 min at 120° C. before the mixture was concentrated in vacuo. To the residue was added water (15 ml) and the mixture was washed with Et2O (3×30 ml). The so purified aq. solution was acidified by the addition of 6 N HCl and extracted with EtOAc (1×30 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (108 mg); MS-(−)-ion M−1=365.1.

Quelle