Trifluoroacetic acid → HCID 59997883, compound

HRID 1717446Notes

Reaction equation

HRID 1717446 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][C@H:19]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])[CH2:18]2)[C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].FC(F)(F)C(O)=O>CCCCCCC>[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][C@H:19]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:32]=[CH:33][C:34]([CH3:37])=[CH:35][CH:36]=4)[O:28][C:29]=3[CH3:30])[CH2:18]2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68505329HCID 68505329, compound2×

Product 1

HCID 59997883HCID 59997883, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

from tert-butyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexyloxymethyl]benzoate: 200 g (396 mmol) of tert-butyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoate are dissolved in n-heptane. 300 g (2.6 mol) of trifluoroacetic acid are added. The reaction is stirred at RT for 24 hours and subsequently concentrated fully by evaporation. The residue is taken up in 1.0 l of diisopropyl ether and washed four time with 500 ml each time of water. Subsequently, 1.0 l of water is added and a basic pH is established by addition of sodium hydroxide solution (4 M). After phase separation, the aqueous phase is washed twice with 400 ml each time of diisopropyl ether. After addition of 1.6 l of diisopropyl ether, the mixture is acidified with hydrochloric acid (2 M). After phase separation, the organic phase is washed four times with 500 ml each time of water and subsequently concentrated to about a third of the volume. 2-methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoic acid precipitates out as a crystalline solid and is filtered off. After drying under reduced pressure, 2-methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoic acid is obtained in 66% yield.

Workup

  1. concentrationsubsequently concentrated fully by evaporation
  2. washwashed four time with 500 ml each time of water
  3. additionSubsequently, 1.0 l of water is added
  4. additiona basic pH is established by addition of sodium hydroxide solution (4 M)
  5. customAfter phase separation
  6. washthe aqueous phase is washed twice with 400 ml each time of diisopropyl ether
  7. additionAfter addition of 1.6 l of diisopropyl ether
  8. customAfter phase separation
  9. washthe organic phase is washed four times with 500 ml each time of water
  10. concentrationsubsequently concentrated to about a third of the volume
  11. custom2-methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoic acid precipitates out as a crystalline solid
  12. filtrationis filtered off
  13. customAfter drying under reduced pressure

Sources & evidence

ORD record
ord-105934da691247659c08140753a8b03d
Source dataset
uspto-grants-2010_09
Patent number
US07803950B2

Reaction notes

Loading…