Water → methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

HRID 1924379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924379
[C:1]([NH:7][NH:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].O.C([O-])(O)=O.[Na+]>O=P(Cl)(Cl)Cl>[CH2:2]([C:1]1[O:10][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[N:8][N:7]=1)[CH2:3][CH:4]=[CH2:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 44549344methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate

Produkt 1

HCID 67519434methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate (from Step 3) was heated at 80° C. for 2 h in POCl3 (0.1 M solution). The mixture was cooled at 0° C. and water was carefully added. Solid NaHCO3 was added until the mixture reached pH 7, then the mixture was extracted with EtOAc and the organic layer dried over Na2SO4 to obtain a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ: 8.42 (d, J 15.7, 1H), 5.88-5.78 (m, 1H), 5.08 (d, J 17.2, 1H), 5.01 (d, J 10.3, 1H), 4.04 (dd, J 7.1, 14.2, 1H), 3.64 (s, 3H), 2.75 (t, J 7.3, 2H), 2.39 (m, 2H), 2.13-2.06 (m, 1H), 0.94 (d, J 3.9, 3H), 0.92 (d, J 3.9, 3H). MS (ES+) C12H19N3O3 requires: 253 found: 254 (M+H+).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialthe organic layer dried over Na2SO4
  3. customto obtain a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-34283cb695d8482d8e4f500ead1b907c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178520B2

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