tert-Butanol → 3-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

HRID 1676143노트

반응식

HRID 1676143 반응식
C([O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[O:13][C:14]([C:17]3[S:18][CH:19]=[C:20]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:21]=3[CH3:22])=[N:15][N:16]=2)=[CH:7][C:6]=1[CH3:27])C=C.C[N+]1([O-])CC[O:32]CC1.[C:36]([OH:40])([CH3:39])([CH3:38])C>CC(C)=O.O.O=[Os](=O)(=O)=O>[CH2:23]([C:20]1[C:21]([CH3:22])=[C:17]([C:14]2[O:13][C:12]([C:8]3[CH:9]=[C:10]([CH3:11])[C:5]([O:4][CH2:38][CH:36]([OH:40])[CH2:39][OH:32])=[C:6]([CH3:27])[CH:7]=3)=[N:16][N:15]=2)[S:18][CH:19]=1)[CH:24]([CH3:26])[CH3:25]

참가 물질

7

반응물 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 673506622-(4-Allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole

생성물 1

HCID 237292443-{4-[5-(4-Isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

To a solution of 2-(4-allyloxy-3,5-dimethyl-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazole (181 mg crude, 0.4 mmol) in a mixture of acetone and water (15:1.5 mL) are added N-methylmorpholine-N-oxide (250 mg, 1.85 mmol) and, subsequently, 2.5% OsO4 in tert.-butanol (0.1 mL). The mixture is stirred at rt for 36 h. The mixture is quenched into diethyl ether (75 mL) and washed with 1M aq. NaOH (50 mL), 1M aq. HCl (30 mL) and brine (20 mL). The organic phase is dried (Na2SO4), filtered and evaporated. The residue is purified by TLC (SiO2, EA-heptane) to give 118 mg of 3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propane-1,2-diol as a white powder; LC-MS: tR=1.00 min, [M+1]+=417.28; 1H NMR (D6-DMSO): δ, 7.70 (s, 2 H) 7.51 (s, 1 H), 4.96 (d, J=5.0 Hz, 1 H), 4.63 (t, J=5.6 Hz, 1 H), 3.68-3.89 (m, 3 H), 3.47 (t, J=5.6 Hz, 2 H), 2.51 (s, 3 H), 2.45 (m, 2 H), 2.33 (s, 6 H), 1.85 (m, 1 H), 0.90 (d, J=6.7 Hz, 6 H).

후처리

  1. customThe mixture is quenched into diethyl ether (75 mL)
  2. washwashed with 1M aq. NaOH (50 mL), 1M aq. HCl (30 mL) and brine (20 mL)
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by TLC (SiO2, EA-heptane)

출처 및 근거

ORD 기록
ord-e10ea9ac67b347f28f9a449dc2d9bb4b
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003800B2

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