HCID 58951514, compound → 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionic acid

HRID 2421223Notes

Reaction equation

HRID 2421223 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:5][C:4]=1[CH2:16][O:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][O:25][C:26]([CH3:35])([CH3:34])[C:27]([O:29]C(C)(C)C)=[O:28])[CH2:19]1)[CH3:2]>FC(F)(F)C(O)=O>[CH2:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:5][C:4]=1[CH2:16][O:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([CH2:24][O:25][C:26]([CH3:34])([CH3:35])[C:27]([OH:29])=[O:28])[CH2:19]1)[CH3:2]

Participants

3

Reactant 1

HCID 58951514HCID 58951514, compound

Product 1

HCID 115320922-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

300 mg of tert-butyl 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]-cyclohexylmethoxy}-2-methylpropionate are left to stand in 1 ml of trifluoroacetic acid at RT overnight. The solution is completely evaporated, water is added to the residue, and the pH is adjusted to 3 with sodium bicarbonate solution. The solution is extracted with ethyl acetate, and the organic phase is washed twice with water, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (dichloromethane/methanol gradient), resulting in 256 mg of 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionic acid as yellow resin.

Workup

  1. customThe solution is completely evaporated
  2. additionwater is added to the residue
  3. extractionThe solution is extracted with ethyl acetate
  4. washthe organic phase is washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (dichloromethane/methanol gradient)
  8. customresulting in 256 mg of 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionic acid as yellow resin

Sources & evidence

ORD record
ord-86fcd285229a4f71a2119079594057d8
Source dataset
uspto-grants-2011_06
Patent number
US07956077B2

Reaction notes

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