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

HRID 1631925
ノート
印刷プレビュー

反応式

HRID 1631925 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66707459{1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e3d53b142d9d437297f6bce22508506f
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791272B2

反応ノート

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