Hydrochloric Acid → {1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester

HRID 1631923ノート

反応式

HRID 1631923 の反応式
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:6]([CH3:20])=[N:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=2)[C:9]=1[CH3:10].[CH2:22]([Mg]Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[C:6]([CH3:20])=[N:7][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([CH:18]([OH:19])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:16][CH:17]=2)[C:9]=1[CH3:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 86661579[1-(4-Formyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester2 回HCID 178418336HCID 178418336、化合物

生成物 1

HCID 66707459{1-[4-(1-Hydroxy-2-phenyl-ethyl)-benzyl]-3,5-dimethyl-1H-pyrazol-4-yl}-acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

[1-(4-Formyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 15.1.1, 500 mg, 1.8 mmol) was dissolved in 5 ml tetrahydrofuran, cooled to −78° C., and benzyl magnesium chloride (1.92 ml, 2 M solution in tetrahydrofuran) was added to the solution. After 30 min at this temperature, the mixture was warmed to room temperature within 12 h, and ice and 4 N aqueous HCl was added to the solution. After dilution with ethyl acetate, the organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by MPLC (silica gel, CH2Cl2/methanol 98:2).

後処理

  1. temperaturethe mixture was warmed to room temperature within 12 h
  2. customAfter dilution with ethyl acetate, the organic layer was separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by MPLC (silica gel, CH2Cl2/methanol 98:2)

出典と根拠

ORDレコード
ord-26cb8e164ab5402485546a06b97c10cd
出典データセット
uspto-grants-2014_07
特許番号
US08791272B2

反応ノート

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