Pyridine → (2,5-Dioxopyrrolidin-1-yl) 6-(3-phenylpropanoylamino)hexanoate

HRID 1454120

反応式

HRID 1454120 の反応式
[C:1](=[O:18])([O:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17])ON1C(=O)CCC1=O.[C:19]([NH:29][CH:30]([CH2:34][CH2:35][CH2:36][CH3:37])C(O)=O)(=[O:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1C=CC=CC=1.C(OCC)(=O)C>C(#N)C>[CH2:13]1[C:12](=[O:17])[N:11]([O:10][C:1]([CH2:37][CH2:36][CH2:35][CH2:34][CH2:30][NH:29][C:19]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:28])=[O:18])[C:15](=[O:16])[CH2:14]1

参加物

6

反応物 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 676246Di(succinimido) carbonateHCID 43386914n-Dihydrocinnamoyl aminocaproic acid

生成物 1

HCID 4056227(2,5-Dioxopyrrolidin-1-yl) 6-(3-phenylpropanoylamino)hexanoate収率 72%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Disuccinimidyl carbonate (155 mg, 604 μmoles) was added to a solution of 31 (159 mg, 604 μmoles) and pyridine (97.7 μL, 1.21 mmoles) in acetonitrile (1 mL). The reaction mixture was stirred at room temperature for 2.5 h, during which the solution became clear and evolved gas. The solution was added to ethyl acetate (5 mL), washed with 1 N HCl (2×1 mL) and saturated aqueous NaHCO3 (2×1 mL), dried over MgSO4, and concentrated in vacuo to yield a colorless oil (156 mg, 433 μmoles, 72%). LRMS: not performed. 1H NMR: spectrum is consistent with the predicted structure.

後処理

  1. washwashed with 1 N HCl (2×1 mL) and saturated aqueous NaHCO3 (2×1 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e4747df65802427ab674e05e93bd9c6b
出典データセット
uspto-grants-2009_01
特許番号
US07476661B2

関連ノート

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