Reaktion #496373

Reaktionsgleichung

MeONa

methanol

1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

(S)-alanine

→

title compound

Ausbeute 70.8%

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

Ausbeute 70.8%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenwas concentrated in vacuo
2. 2
   workup.ADDITIONTo the residue was added water (10 mL)
3. 3
   Waschenthe mixture was washed with diethyl ether (4×40 mL)
4. 4
   workup.ADDITIONThe pH of the purified solution was adjusted to about 2 by the addition of aqueous 6 N HCl
5. 5
   ExtraktionThe resulting suspension was extracted with ethyl acetate (1×40 mL)
6. 6
   TrocknenThe organic phase was dried over MgSO4
7. 7
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (135 mg, 0.5 mmol, see Example 1(a)), (S)-alanine (225 mg, 2.5 mmol) and a 0.5 N solution of MeONa in methanol (5 mL, 2.5 mmol) was heated in a microwave oven with stirring for 40 min at 120° C. before the mixture was concentrated in vacuo. To the residue was added water (10 mL) and the mixture was washed with diethyl ether (4×40 mL). The pH of the purified solution was adjusted to about 2 by the addition of aqueous 6 N HCl. The resulting suspension was extracted with ethyl acetate (1×40 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish solid (101 mg); MS-(−)-ion: M−1=284.1.

Quelle