(Tert-butoxycarbonyl)aspartic acid → 3-(Boc-amino)dihydrofuran-2,5-dione

HRID 1435952

Reaktionsgleichung

Reaktionsgleichung von HRID 1435952
[C:1]([O:5][C:6]([NH:8][CH:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][C:11](=[O:13])[O:16][C:14]1=[O:15])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 302432(Tert-butoxycarbonyl)aspartic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 37577793-(Boc-amino)dihydrofuran-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1 g (4.29 mmol) of N-(tert-butoxycarbonyl)-DL-aspartic acid and 0.98 g (5.15 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) in 100 mL of DCM, was stirred at room temperature overnight. The solution was extracted three times with 5% aq. NaHSO4, the organic extracts were dried over anh. sodium sulfate and the solvent evaporated under vacuum. In this way 750 mg of the title compound were recovered. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.38 (s, 9 H) 2.78-2.90 (m, 1 H) 3.15-3.28 (m, 1 H) 4.54-4.65 (m, 1 H) 7.73 (d, J=7.91 Hz, 1 H).

Aufarbeitung

  1. extractionThe solution was extracted three times with 5% aq. NaHSO4
  2. dry with materialthe organic extracts were dried over anh. sodium sulfate
  3. customthe solvent evaporated under vacuum
  4. customIn this way 750 mg of the title compound were recovered

Quellen und Nachweise

ORD-Eintrag
ord-441468b8f1794221b684e37447bc2130
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618982B2

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