Glycine → Glycine, N-[[4-hydroxy-7-(phenylthio)-3-isoquinolinyl]carbonyl]-
Reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:12]=2)=[O:7])CCC.[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C[O-].[Na+].CO>>[OH:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([S:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9][C:8]=1[C:6]([NH:26][CH2:27][C:28]([OH:30])=[O:29])=[O:7]Participants
Procedure
A mixture of 113 mg of 4-hydroxy-7-phenylsulfanyl-isoquinoline-3-carboxylic acid butyl ester (0.32 mmol), 244 mg of glycine (3.2 mmol), and 6.4 ml of a 0.5 N solution of sodium methoxide in methanol (3.2 mmol) was refluxed for 24 h with stirring. Then the solvent was evaporated in vacuo, the residue dissolved in 25 ml of water and the resulting solution was washed twice with 50 ml of ethyl acetate. The pH of the solution was subsequently adjusted to about 3 by addition of concentrated hydrochloric acid and the resulting slurry was extracted twice with 25 ml of ethyl acetate. The combined extracts were dried over MgSO4 and evaporated in vacuo. 103 mg of the title compound were obtained; 1H NMR (DMSO-d6): δ=9.32 (t, 1 H), 8.74 (s, 1 H), 8.19 (d, 1 H), 7.94 (d, 1 H), 7.45 to 7.65 (m, 6 H), 4.02 (d, 2 H).
Workup
- temperaturewas refluxed for 24 h
- customThen the solvent was evaporated in vacuo
- dissolutionthe residue dissolved in 25 ml of water
- washthe resulting solution was washed twice with 50 ml of ethyl acetate
- additionThe pH of the solution was subsequently adjusted to about 3 by addition of concentrated hydrochloric acid
- extractionthe resulting slurry was extracted twice with 25 ml of ethyl acetate
- dry with materialThe combined extracts were dried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-71a21475d84f45db8d888e2bd146d5a7
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916585B2
Reaction notes
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