Glycine → 2-(1-Cyano-4-hydroxyisoquinoline-3-carboxamido)acetic 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][CH2:22][C:23]([OH:25])=[O:24].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][CH2:22][C:23]([OH:25])=[O:24])=[O:7])[N:9]=1)#[N:20]Participants
5
Procedure
A mixture of 1-cyano-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (89 mg, 0.33 mmol), glycine (375 mg, 5 mmol), and a 0.5 N solution of MeONa in MeOH (8 mL, 4 mmol) was refluxed with stirring for 48 h before it was concentrated in vacuo. The residue was dissolved in water (20 mL). The solution was washed with diethyl ether before its pH was adjusted to 2 to 3 by addition of aqueous 6 N HCl. The resulting suspension was extracted with ethyl acetate (1×30 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish solid (72 mg); MS-(−)-ion: M−1=270.2.
Workup
- concentrationwas concentrated in vacuo
- dissolutionThe residue was dissolved in water (20 mL)
- washThe solution was washed with diethyl ether before its pH
- additionwas adjusted to 2 to 3 by addition of aqueous 6 N HCl
- extractionThe resulting suspension was extracted with ethyl acetate (1×30 mL)
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-540b235693db4c5da45c61c83466af41
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759373B2
Reaction notes
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