Water → HCID 57682953, compound

HRID 494314Notes

Reaction equation

HRID 494314 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][O:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1.[H-].[Na+].[CH2:23]([C:25]1[O:29][C:28]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)=[N:27][C:26]=1[CH2:40]I)[CH3:24].O>CC(OC)(C)C>[CH2:23]([C:25]1[O:29][C:28]([C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:39])[F:37])=[CH:34][CH:35]=2)=[N:27][C:26]=1[CH2:40][O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([CH2:9][O:10][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 57682962HCID 57682962, compoundHCID 57682971HCID 57682971, compound

Product 1

HCID 57682953HCID 57682953, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

300 mg of tert-butyl 2-((1R,3S)-3-hydroxymethylcyclohexylmethoxy)-2-methylpropionate are dissolved in 10 ml of MTBE, and 50 mg of sodium hydride (60% in mineral oil) are added. After gas evolution ceases, 600 mg of 5-ethyl-4-iodomethyl-2-(4-trifluoromethylphenyl)oxazole are added, and the suspension is heated under reflux overnight. After addition of water and MTBE, the phases are separated, and the organic phase is washed with saturated sodium chloride solution, dried over MgSO4 and concentrated. The residue is purified by preparative HPLC, resulting in 190 mg of tert-butyl 2-{(1S,3R)-3-[5-ethyl-2-(4-trifluoromethylphenyl)oxazol-4-ylmethoxymethyl]-cyclohexylmethoxy}-2-methylpropionate as yellow oil.

Workup

  1. temperaturethe suspension is heated
  2. temperatureunder reflux overnight
  3. customthe phases are separated
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by preparative HPLC
  8. customresulting in 190 mg of tert-butyl 2-{(1S,3R)-3-[5-ethyl-2-(4-trifluoromethylphenyl)oxazol-4-ylmethoxymethyl]-cyclohexylmethoxy}-2-methylpropionate as yellow oil

Sources & evidence

ORD record
ord-696f86a5946d4a02acb22906fb3bcebb
Source dataset
uspto-grants-2009_05
Patent number
US07538131B2

Reaction notes

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