Ethyl Acetate → 1-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-hydroxymethyl-phenyl)urea

HRID 499195

反応式

HRID 499195 の反応式
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[N:16]([CH3:24])[N:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:19]=2)=[O:13])=[CH:7][CH:6]=1)C.CC(C[AlH]CC(C)C)C.C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:20]([C:18]1[CH:19]=[C:15]([NH:14][C:12]([NH:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)=[O:13])[N:16]([CH3:24])[N:17]=1)([CH3:23])([CH3:21])[CH3:22]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 14487Diisobutylaluminum hydrideHCID 594208944-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]benzoic acid ethyl ester

生成物 1

HCID 594208851-(5-tert-Butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-hydroxymethyl-phenyl)urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a dry flask is added 872 mg (2.5 mmol) of 4-[3-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-ureido]-benzoic acid ethyl ester in 30 mL dry methylene chloride and cooled to 0° C. Next, 10.12 mL of 1M DIBAL in hexanes (4 eq., 10.12 mmol) is added and the reaction is allowed to reach room temperature. The mixture is then stirred for 1 hour, and 60 mL of ethyl acetate and 100 mL of sodium tartrate saturated aqueous solution are added, and the mixture is stirred for another 30 min. Then the organic layer is separated and washed with water and dried over magnesium sulfate, filtered, and evaporated to a white solid weighing 720 mg (2.4 mmoles, 95%, ES+(m/z) 303 [M+H]).

後処理

  1. customto reach room temperature
  2. stirringthe mixture is stirred for another 30 min
  3. customThen the organic layer is separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a white solid

出典と根拠

ORDレコード
ord-ef847b99baa64e74be6f19788bbd3d59
出典データセット
uspto-grants-2010_08
特許番号
US07767674B2

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