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

HRID 1393180노트

반응식

HRID 1393180 반응식
[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

참가 물질

8

반응물 5

HCID 8058HexaneHCID 11644ChloroiodomethaneHCID 25517Ammonium Chloride2회HCID 10294976(Z)-1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)-2-propenyl]ureaHCID 178418750HCID 178418750, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cd50d9dfa4c548cd906b3baf855403f1
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345064B2

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