Methanol → (S)-2-(1-Cyano-4-hydroxyisoquinoline-3-carboxamido)propanoic acid
Reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:19]#[N:20])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:21][C@H:22]([C:24]([OH:26])=[O:25])[CH3:23].CO[Na].CO>>[C:19]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:21][C@@H:22]([CH3:23])[C:24]([OH:26])=[O:25])=[O:7])[N:9]=1)#[N:20]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
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.
Workup
- concentrationwas concentrated in vacuo
- additionTo the residue was added water (10 mL)
- washthe mixture was washed with diethyl ether (4×40 mL)
- additionThe pH of the purified solution was adjusted to about 2 by the addition of aqueous 6 N HCl
- extractionThe resulting suspension was extracted with ethyl acetate (1×40 mL)
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c15b97bfc43f430faa39cde959c5b9a7
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759373B2
Reaction notes
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