Hexane → cis-1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]urea

HRID 11476

反応式

HRID 11476 の反応式
[CH2:1]([Zn]CC)C.CCCCCC.ClCI.[C:15]12([CH2:25][CH2:26][N:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:28]([NH:30][CH2:31]/[CH:32]=[CH:33]\[C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)=[O:29])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2.[Cl-].[NH4+]>ClCCCl.C(OCC)(=O)C>[C:15]12([CH2:25][CH2:26][N:27]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:28]([NH:30][CH2:31][C@@H:32]3[CH2:1][C@@H:33]3[C:34]3[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=3)=[O:29])[CH2:16][CH:17]3[CH2:18][CH:19]([CH2:20][CH:21]([CH2:23]3)[CH2:22]1)[CH2:24]2

参加物

8

反応物 5

HCID 8058HexaneHCID 11644ChloroiodomethaneHCID 25517Ammonium Chloride2 回HCID 10294976(Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]ureaHCID 178418750HCID 178418750、化合物

生成物 1

HCID 67118730cis-1-[2-(1-Adamantyl)ethyl]-1-pentyl-3-[2-(4-pyridyl)cyclopropylmethyl]urea収率 3.5%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 1.0 M solution of diethylzinc in hexane (3.1 ml, 3.1 mmol) and chloroiodomethane (0.44 ml, 6.1 mol) were added to a solution of (Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]urea (Compound No. 1-111) in anhydrous 1,2-dichloroethane (3 ml) under a nitrogen atmosphere and ice-cooling, and the mixture was stirred for one hour. A saturated aqueous ammonium chloride solution (10 ml) was added to the reaction mixture under ice-cooling, and the whole was stirred at room temperature for 20 minutes and distributed with ethyl acetate (20 ml) and a saturated aqueous ammonium chloride solution (10 ml). The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 9.0 mg (3.5%) of the titled compound as colorless crystals.

後処理

  1. temperatureice-cooling
  2. temperaturecooling
  3. stirringthe whole was stirred at room temperature for 20 minutes
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b777ff91edf849818303f364dcaebf2f
出典データセット
uspto-grants-2006_08
特許番号
US07098226B2

関連ノート

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