Trifluoroacetic acid → 2-{cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl-methoxy}-2-methylpropionic acid

HRID 854650Notes

Reaction equation

HRID 854650 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([CH2:21][O:22][C:23]([CH3:32])([CH3:31])[C:24]([O:26]C(C)(C)C)=[O:25])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([CH2:21][O:22][C:23]([CH3:31])([CH3:32])[C:24]([OH:26])=[O:25])[CH2:16]3)[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69240928Tert-butyl 2-{cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-yl-methoxy]cyclohexylmethoxy}-2-methylpropionate

Product 1

HCID 692438722-{cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl-methoxy}-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.07 g of tert-butyl 2-{cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-yl-methoxy]cyclohexylmethoxy}-2-methylpropionate is dissolved in 1 ml of dichloromethane, 1 ml of trifluoroacetic acid is added and the mixture is stirred at room temperature. The reaction is monitored (LCMS), showing complete conversion after 30 minutes. The reaction mixture is extracted with water/dichloromethane and, after removal of the solvent under reduced pressure, purified by preparative HPLC. This gives 0.06 g of the carboxylic acid 2-{cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]-cyclohexylmethoxy}-2-methylpropionic acid as a colorless oil.

Workup

  1. customafter 30 minutes
  2. extractionThe reaction mixture is extracted with water/dichloromethane
  3. customafter removal of the solvent under reduced pressure
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-0f8c867b72a94ab8b27bcaa866db90f5
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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