Tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate → 2-[cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionic acid

HRID 854646Notes

Reaction equation

HRID 854646 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][O:23][C:24]([CH3:33])([CH3:32])[C:25]([O:27]C(C)(C)C)=[O:26])[CH2:17]1>FC(F)(F)C(O)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:14][O:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][C@H:18]([CH2:22][O:23][C:24]([CH3:33])([CH3:32])[C:25]([OH:27])=[O:26])[CH2:17]1

Participants

3

Reactant 1

HCID 69242284Tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate

Product 1

HCID 688637322-[cis-3-(5-Methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionic acidYield 37.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg of tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclo-hexylmethoxy]-2-methylpropionate are stirred in 2 ml of trifluoroacetic acid for 1 h. The solution is concentrated completely and purified by flash chromatography (heptane/ethyl acetate 5/1) giving 66 mg of 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionic acid.

Workup

  1. concentrationThe solution is concentrated completely
  2. custompurified by flash chromatography (heptane/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-7e3868c40f324bf5ac6323dc9effe0e5
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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