Amantadine → 2-[N'(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide

HRID 11442

반응식

HRID 11442 반응식
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]([OH:15])=O)[CH2:9][CH2:10][CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]12([NH2:26])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:16]12([NH:26][C:13](=[O:15])[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH3:11])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2

참가 물질

5

반응물 3

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 121366292-(((Tert-butoxy)carbonyl)(propyl)amino)acetic acid

생성물 1

HCID 121366302-[N'(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Next, methylene chloride (208 ml) was added to a mixture of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid (4.52 g, 20.8 mmol) and 1-adamantaneamine (3.46 g, 22.9 mmol), and the whole was stirred at room temperature. N,N-Diisopropylethylamine (7.25 ml, 41.6 mmol) and then O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate (8.71 g, 22.9 mmol) were added thereto, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 7.88 g (quantitatively) of 2-[N-(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide as a colorless oily matter. The obtained oily matter solidified at room temperature.

후처리

  1. stirringthe whole was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-352b45ba8a4c4cccbe141dd427679355
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098226B2

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