Sodium Methoxide → (S)-1-{4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-3-methoxy-propan-2-ol

HRID 2047334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047334
[CH2:1]([N:3]([CH2:30][CH3:31])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@H:24]4[CH2:26][O:25]4)=[C:17]([CH2:27][CH3:28])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:29])[N:5]=1)[CH3:2].[CH3:32][O-:33].[Na+]>CO.CC(=O)OCC>[CH2:30]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:23][C@@H:24]([OH:25])[CH2:26][O:33][CH3:32])=[C:17]([CH2:27][CH3:28])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:29])[N:5]=1)[CH3:31]

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 86640600HCID 86640600, Verbindung

Produkt 1

HCID 68579274(S)-1-{4-[5-(2-Diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-3-methoxy-propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of diethyl-{4-[3-((S)-3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridin-2-yl}-amine (100 mg, 0.229 mmol) in 5.4 M NaOMe in methanol (5 mL) is stirred at 70° C. for 72 h. The mixture is diluted with EA and washed with water and brine. The org. extract is dried over Na2SO4, filtered and concentrated. The crude product is purified on prep. TLC plates with heptane:EA 1:1 to give the title compound (91 mg) as a yellow solid; LC-MS*: tR=1.21 min, [M+1]+=455.09; 1H NMR (CDCl3): δ 1.25 (t, J=7.0 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 2.41 (s, 3H), 2.50 (s, 3H), 2.58 (d, J=5.0 Hz, 1H), 2.77 (q, J=7.8 Hz, 2H), 3.47 (s, 3H), 3.59-3.70 (m, 6H), 3.92 (d, J=5.3 Hz, 2H), 4.19-4.27 (m, 1H), 7.01 (s, 1H), 7.10 (s, 1H), 7.87 (s, 1H), 7.88 (s, 1H).

Aufarbeitung

  1. washwashed with water and brine
  2. extractionextract
  3. dry with materialis dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified on prep

Quellen und Nachweise

ORD-Eintrag
ord-f5d7c41b65be48bcaf31ce25e60df73e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592460B2

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