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

HRID 18385
ノート
印刷プレビュー

反応式

HRID 18385 の反応式
[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.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 2130AmantadineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 121366292-(((Tert-butoxy)carbonyl)(propyl)amino)acetic acid

生成物 1

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

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

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 O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (8.71 g, 22.9 mmol) were added thereto successively, and the whole was stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was separated by silica gel column chromatography to give 2-[N′-(t-butoxycarbonyl)-N′-propylamino]acetic acid N-(1-adamantyl)amide (7.88 g, quantitatively) as a colorless oily matter. The obtained oily matter solidified at room temperature.

後処理

  1. stirringsuccessively, and the whole was stirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was separated by silica gel column chromatography

出典と根拠

ORDレコード
ord-4cf23e47c95b49a18e490900848745d3
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741346B2

反応ノート

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