Tetrahydrofuran → 4-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine

Reaction equation

[CH2:1]([O:8][C:9]1[C:31]([CH3:32])=[CH:30][C:12]([C:13]([NH:15][CH2:16][C:17]([C:19]2[CH:24]=C(C)N=C(CC(C)C)[CH:20]=2)=[O:18])=O)=[CH:11][C:10]=1[CH2:33][CH3:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+:37](S(N=C(OC)[O-])(=O)=O)([CH2:40][CH3:41])[CH2:38][CH3:39].[CH2:50]1[CH2:54]OC[CH2:51]1>>[CH2:1]([O:8][C:9]1[C:31]([CH3:32])=[CH:30][C:12]([C:13]2[O:18][C:17]([C:19]3[CH:20]=[C:38]([CH3:39])[N:37]=[C:40]([CH2:41][CH:50]([CH3:54])[CH3:51])[CH:24]=3)=[CH:16][N:15]=2)=[CH:11][C:10]=1[CH2:33][CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamate2×

HCID 685527854-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide

Product 1

HCID 685539084-[2-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine

Procedure

To a solution 4-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide (70 mg, 0.153 mmol) in THF (2 mL), Burgess reagent (95 mg, 0.377 mmol) is added and the mixture is refluxed for 2 h. Another portion of Burgess reagent (50 mg, 0.231 mmol) is added and stirring is continued at rt for 16 h. The solvent is evaporated and the crude product is purified on prep. TLC with heptane:EA 1:2 to give 4-[2-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-oxazol-5-yl]-2-isobutyl-6-methyl-pyridine (24 mg) as a yellow oil; LC-MS: tR=1.33*, [M+1]+=441.04.