Lithium hydroxide, monohydrate → (R)-3-hydroxy-4-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-oxobutanoic acid

HRID 2062218노트

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[OH:1][C@@H:2]([C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([CH3:26])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[OH:33])[N:17]=2)[CH2:12][CH2:11]1)=[O:9])[CH2:3][C:4]([O:6]C)=[O:5].O[Li].O>C1COCC1.O>[OH:1][C@@H:2]([C:8]([N:10]1[CH2:11][CH2:12][N:13]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([CH3:26])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[OH:33])[N:17]=2)[CH2:14][CH2:15]1)=[O:9])[CH2:3][C:4]([OH:6])=[O:5]

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실험 절차

(R)-Methyl 3-hydroxy-4-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-oxobutanoate (88 mg, 0.20 mmol) and LiOH.H2O (33 mg, 0.78 mmol) were stirred in THF:H2O 1:1 at room temperature for 3 h. After acidification with 1 M HCl and extraction with EtOAc, the organic extracts were washed with water, dried over Na2SO4, and concentrated. The crude material was then purified via silica gel chromatography using 0-10% MeOH/CH2Cl2 to obtain (R)-3-hydroxy-4-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-oxobutanoic acid (75 mg, 88%). LC/MS: m/z 437.3 (M+H)+ at 2.04 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

extractionAfter acidification with 1 M HCl and extraction with EtOAc
washthe organic extracts were washed with water
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude material was then purified via silica gel chromatography

출처 및 근거

ORD 기록: ord-22e018e882104a58851975e0a297e5a4
출처 데이터셋: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08283354B2

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