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

HRID 1672431

Reaktionsgleichung

Reaktionsgleichung von HRID 1672431
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f3f793936cbd45aea6cf8e5f030c3504
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998946B2

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