4-{3-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-(1-ethyl-propyl)-6-methoxy-pyridine → (S)-3-(2-Ethyl-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diol

HRID 245101Notes

Reaction equation

HRID 245101 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]3[N:20]=[C:19]([C:21]4[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH:22]=4)[O:18][N:17]=3)=[CH:11][C:10]=2[CH2:34][CH3:35])[CH2:4][O:3]1>Cl.O1CCOCC1>[CH2:34]([C:10]1[CH:11]=[C:12]([C:16]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([CH:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH:22]=3)[O:18][N:17]=2)[CH:13]=[C:14]([CH3:15])[C:9]=1[O:8][CH2:7][C@@H:5]([OH:6])[CH2:4][OH:3])[CH3:35]

Participants

4

Reactant 1

HCID 674914894-{3-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-(1-ethyl-propyl)-6-methoxy-pyridine

Product 1

HCID 49871885(S)-3-(2-Ethyl-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-propane-1,2-diolYield 33.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-{3-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-phenyl]-[1,2,4]oxadiazol-5-yl}-2-(1-ethyl-propyl)-6-methoxy-pyridine (250 mg, 504 μmol) in 4 M HCl in dioxane (10 mL) is stirred at rt for 90 min before it is concentrated. The crude product is purified on prep. TLC plates using DCM containing 10% of methanol to give the title compound (76 mg) as a pale brownish solid; LC-MS: tR=1.12 min, [M+H]+=456.12; 1H NMR (CDCl3): δ0.85 (t, J=7.0 Hz, 6H), 1.33 (t, J=7.0 Hz, 3H), 1.70-1.89 (m, 4H), 2.42 (s, 3H), 2.61-2.71 (m, 1H), 2.78 (q, J=7.3 Hz, 2H), 3.82-4.00 (m, 4H), 4.04 (s, 3H), 4.14-4.21 (m, 1H), 7.34 (s, 1H), 7.46 (s, 1H), 7.86-7.91 (m, 2H).

Workup

  1. concentrationis concentrated
  2. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-ad242c2b5a284c779309233f071e9623
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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