聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 2-{[5-(3-Chlorophenyl)-3-hydroxypyridine-2-carbonyl]-amino}-2-methyl-propionic acid

HRID 1908299笔记

反应方程式

HRID 1908299 反应方程式
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

参与物

5

反应物 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 3939氢氧化锂HCID 248911462-{[5-(3-Chlorophenyl)-3-hydroxy-pyridine-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester

产物 1

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

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

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 (1H, br s), 12.25 (1H, s), 9.05 (1H, s), 8.53 (1H, d, J=2.0 Hz), 7.91 (1H, s), 7.74-7.83 (2H, m), 7.51-7.58 (2H, m), 1.58 (6H, s). HPLC-MS: m/z 335 [M+H]+.

后处理

  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

来源与证据

ORD记录
ord-07705c3e05294736a88f1de45b250af5
来源数据集
uspto-grants-2013_12
专利号
US08598210B2

反应笔记

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