(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 2040816노트

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HRID 2040816 반응식
[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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1d3e61f64b7d48d0831f6e32cc120965
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580824B2

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