Water → 2-{[5-(3-Chlorophenyl)-3-hydroxypyridine-2-carbonyl]-amino}-2-methyl-propionic acid

HRID 1798001ノート

反応式

HRID 1798001 の反応式
C[O:2][C:3](=[O:24])[C:4]([NH:7][C:8]([C:10]1[C:15]([OH:16])=[CH:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:12][N:11]=1)=[O:9])([CH3:6])[CH3:5].[Li+].[OH-].O>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([C:13]2[CH:14]=[C:15]([OH:16])[C:10]([C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:24])=[O:2])=[O:9])=[N:11][CH:12]=2)[CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 248911462-{[5-(3-Chlorophenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester

生成物 1

HCID 248910912-{[5-(3-Chlorophenyl)-3-hydroxypyridine-2-carbonyl]-amino}-2-methyl-propionic acid収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-{[5-(3-chlorophenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester, 20, (0.082 g, 0.24 mmol) in THF (4 mL) is added LiOH (0.024 g, 0.98 mmol) and H2O (1 mL) and the resulting solution stirred for 3 days at room temperature. The solvent is removed under reduced pressure and the pale yellow solid that remains is then acidified with 1M HCl to until the pH is approximately 1 and the solution extracted twice with EtOAc. The combined organic layers are combined, dried (Na2SO4), filtered and concentrated under reduced pressure to afford 0.064 g (81% yield) of the desired compound as a white solid. 1H NMR (250 MHz, DMSO-d6) δ ppm 12.99 (1 H, br s), 12.25 (1 H, s), 9.05 (1 H, s), 8.53 (1 H, d, J=2.0 Hz), 7.91 (1 H, s), 7.74-7.83 (2 H, m), 7.51-7.58 (2 H, m), 1.58 (6 H, s). HPLC-MS: m/z 335 [M+H]+.

後処理

  1. customThe solvent is removed under reduced pressure
  2. extractionthe solution extracted twice with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-36f340b0f6ea407e990fc29720f45319
出典データセット
uspto-grants-2013_01
特許番号
US08343952B2

反応ノート

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