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

반응식

[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]

참가 물질

반응물 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

생성물 1

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

실험 절차

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).