(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate → 4-{3-[4-(2,2-Dimethyl-[1,3]dioxan-5-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-isobutyl-6-methyl-pyridine

HRID 2040816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040816
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].[CH3:27][C:28]1([CH3:40])[O:33][CH2:32][CH:31]([CH2:34]OS(C)(=O)=O)[CH2:30][O:29]1>C(O)(C)C.[OH-].[Na+].CC(=O)OCC>[CH3:27][C:28]1([CH3:40])[O:33][CH2:32][CH:31]([CH2:34][O:26][C:4]2[C:5]([CH3:25])=[CH:6][C:7]([C:9]3[N:13]=[C:12]([C:14]4[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([CH2:21][CH:22]([CH3:23])[CH3:24])[CH:15]=4)[O:11][N:10]=3)=[CH:8][C:3]=2[CH2:1][CH3:2])[CH2:30][O:29]1

Komponenten

6

Edukt 2

HCID 10998661(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonateHCID 1359239042-Ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol

Produkt 1

HCID 685526404-{3-[4-(2,2-Dimethyl-[1,3]dioxan-5-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-isobutyl-6-methyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol (200 mg, 0.569 mmol) in isopropanol (10 mL) and 3 N aq. NaOH (3 mL), methanesulfonic acid 2,2-dimethyl-[1,3]dioxan-5-ylmethyl ester (290 mg, 1.71 mmol) is added. The mixture is stirred at 60° C. for 24 h. The mixture is diluted with EA and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with heptane:EA 3:1 to give 4-{3-[4-(2,2-dimethyl-[1,3]dioxan-5-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-isobutyl-6-methyl-pyridine which is dissolved in THF (5 mL), water (0.5 mL) and TFA (0.25 mL). The solution is stirred at rt for 1 h before the solvent is evaporated. The remaining residue is separated by chromatography on prep. TLC plates with DCM containing 10% of MeOH to give 2-{2-ethyl-4-[5-(2-isobutyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxymethyl}-propane-1,3-diol (20 mg) as a colourless oil; LC-MS: tR=0.86 min, [M+1]+=440.12.

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3 solution
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography on prep

Quellen und Nachweise

ORD-Eintrag
ord-1d3e61f64b7d48d0831f6e32cc120965
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580824B2

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