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

HRID 2062218ノート

反応式

HRID 2062218 の反応式
[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]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 136121665(R)-methyl 3-hydroxy-4-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-oxobutanoate

生成物 1

HCID 136121458(R)-3-hydroxy-4-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-4-oxobutanoic acid収率 88%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

(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)).

後処理

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

出典と根拠

ORDレコード
ord-22e018e882104a58851975e0a297e5a4
出典データセット
uspto-grants-2012_10
特許番号
US08283354B2

反応ノート

読み込み中…