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

HRID 1454120

반응식

HRID 1454120 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e4747df65802427ab674e05e93bd9c6b
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476661B2

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