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盐酸 → [3,5-Dimethyl-1-(4-phenylacetyl-benzyl)-1H-pyrazol-4-yl]-acetic acid

HRID 1631925
笔记
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反应方程式

HRID 1631925 反应方程式
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:6]([CH3:27])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([OH:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[C:9]=1[CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+].Cl>ClCCl.O1CCOCC1.O>[CH3:27][C:6]1[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[C:9]([CH3:10])[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:16][CH:17]=2)[N:7]=1
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

8

反应物 4

HCID 313盐酸HCID 14798氢氧化钠HCID 159087戴斯-马丁氧化剂HCID 66707459{1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester2 次

产物 1

HCID 58071788[3,5-Dimethyl-1-(4-phenylacetyl-benzyl)-1H-pyrazol-4-yl]-acetic acid

试剂、催化剂与溶剂 3

HCID 962
聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 6344二氯甲烷溶剂
HCID 312751,4-二氧六环溶剂

反应条件

温度
0 °C

实验过程

Oxidation: {1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester (intermediate 15.1.2, 100 mg, 0.26 mmol) was dissolved in 4 ml dichloromethane, cooled to 0° C. and Dess-Martin periodinane (135 mg, 0.32 mmol) was added to the solution. After warming to room temperature, the mixture was stirred for 3 h. The solvent was evaporated under reduced pressure. Saponification: The ester intermediate (70 mg, 0.19 mmol) was dissolved in 2 ml dioxane and aqueous NaOH solution (0.37 ml, 1 M). After stirring for 2.5 h at 60° C. and dilution with water, aqueous HCl solution (0.39 ml, 1 M) was added. The mixture was extracted with ethyl acetate, and the organic layer was dried with MgSO4 and evaporated under reduced pressure. The residue was purified by preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

后处理

  1. temperatureAfter warming to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. stirringAfter stirring for 2.5 h at 60° C.
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried with MgSO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3)

来源与证据

ORD记录
ord-e3d53b142d9d437297f6bce22508506f
来源数据集
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08791272B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记