Glycine → {[7-Hydroxy-3-(4-methoxy-phenyl)-4-pyrazol-1-ylmethyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid

反応式

[N:1]1([CH2:6][C:7]2[C:12]3[C:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)=[N:14][O:15][C:11]=3[C:10]([OH:24])=[C:9]([C:25](OCC)=[O:26])[N:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[NH2:30][CH2:31][C:32]([OH:34])=[O:33].C[O-].[Na+]>>[OH:24][C:10]1[C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:12]=2[C:7]([CH2:6][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:8][C:9]=1[C:25]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:26]

参加物

反応物 3

HCID 750Glycine

HCID 10942334Sodium Methoxide

HCID 67529978Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate

生成物 1

HCID 42633436{[7-Hydroxy-3-(4-methoxy-phenyl)-4-pyrazol-1-ylmethyl-isoxazolo[4,5-c]pyridine-6-carbonyl]-amino}-acetic acid収率 68.9%

実験手順

Ethyl 4-((1H-pyrazol-1-yl)methyl)-7-hydroxy-3-(4-methoxyphenyl)isoxazolo[4,5-c]pyridine-6-carboxylate (19 mg, 0.048 mmol) and glycine (181 mg, 2.41 mmol) were added to sodium methoxide solution (3.6 mL, 1.81 mmol, 0.5 M in MeOH) and the mixture was refluxed for 3 days. The mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in 10 mL of water, and washed with EtOAc. The aqueous layer was acidified to pH 3 with 4M hydrochloric acid and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give 14 mg of the title compound. MS: (+) m/z 424.31 (M+1).