Glycine → ([1-(4-Acetylamino-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino)-acetic acid

反応式

C(O[C:6]([C:8]1[N:9]=[C:10]([O:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=2)[C:11]2[C:16]([C:17]=1[O:18]C(=O)C)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:33][CH2:34][C:35]([OH:37])=[O:36].C[O-].[Na+].CO>>[C:30]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]([OH:18])=[C:8]([C:6]([NH:33][CH2:34][C:35]([OH:37])=[O:36])=[O:7])[N:9]=2)=[CH:28][CH:27]=1)(=[O:32])[CH3:31]

参加物

反応物 4

HCID 750Glycine

HCID 887Methanol

HCID 10942334Sodium Methoxide

HCID 667129554-Acetoxy-1-(4-acetylamino-phenoxy)-isoquinoline-3-carboxylic acid butyl ester

生成物 1

HCID 11200275([1-(4-Acetylamino-phenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino)-acetic acid収率 64%

実験手順

A mixture of 4-Acetoxy-1-(4-acetylamino-phenoxy)-isoquinoline-3-carboxylic acid butyl ester (150 mg, 0.34 mmol), glycine (290 mg, 3.4 mmol), and 7.8 ml of a 0.5N solution of sodium methoxide in methanol (3.9 mmol) was refluxed over the weekend with stirring. Then the solvent was evaporated in vacuo and the residue dissolved in 25 ml of water. The pH of the solution was subsequently adjusted to about 2 and the resulting slurry was extracted with ethyl acetate (3×30 ml). The combined extracts were dried over MgSO4 and evaporated in vacuo. Recrystallization of the residue from methanol/CH2Cl2 gave 86 mg of the title compound; MS-(+)-ion: M+1=396.15.