Ethyl Acetate → HCID 58951514, compound

HRID 2421222Notes

Reaction equation

HRID 2421222 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][O:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.[H-].[Na+].I[CH2:23][C:24]1[N:25]=[C:26]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)[O:27][C:28]=1[CH2:29][CH3:30].C(OCC)(=O)C>CC(OC)(C)C>[CH2:29]([C:28]1[O:27][C:26]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)=[N:25][C:24]=1[CH2:23][O:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH2:8][O:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1)[CH3:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 574345064-Iodomethyl-5-ethyl-2-(3-methoxyphenyl)oxazoleHCID 58951512HCID 58951512, compound

Product 1

HCID 58951514HCID 58951514, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent4×

Procedure

200 mg of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpropionate are added dropwise as solution in MTBE to a suspension of 65 mg of sodium hydride (60% by weight in mineral oil) in 10 ml of MTBE. After gas evolution ceases, 503 mg of 4-iodomethyl-5-ethyl-2-(3-methoxyphenyl)oxazole are added as solution in MTBE, and the suspension is heated under reflux overnight. Ethyl acetate (MTBE can also be used) is added to the reaction mixture, and the mixture is washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate gradient), resulting in 323 mg of tert-butyl 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionate as yellow oil.

Workup

  1. temperaturethe suspension is heated
  2. temperatureunder reflux overnight
  3. additionis added to the reaction mixture
  4. washthe mixture is washed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate gradient)
  8. customresulting in 323 mg of tert-butyl 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionate as yellow oil

Sources & evidence

ORD record
ord-62b22e9b7ce2458c89cbbbb149e84a96
Source dataset
uspto-grants-2011_06
Patent number
US07956077B2

Reaction notes

Loading…