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

HRID 2040832Notes

Reaction equation

HRID 2040832 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

4

Reactant 3

HCID 8028TetrahydrofuranHCID 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.

Workup

  1. temperaturethe mixture is refluxed for 2 h
  2. customThe solvent is evaporated
  3. customthe crude product is purified on prep

Sources & evidence

ORD record
ord-50020277fcfa4d1bb679398644e96edc
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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