Methanol → HCID 15840441, compound

Reaction equation

C(O[N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[C:15]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:14]=2)[CH2:8][C:7]1=C=O)(C)(C)C.[OH-:32].[Na+].[CH3:34][OH:35]>>[C:16]([O:32][C:34]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[C:15]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])[CH:14]=2)[CH2:10][CH2:11]1)=[O:35])([CH3:19])([CH3:17])[CH3:15]

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 86754650HCID 86754650, compound

Product 1

HCID 15840441HCID 15840441, compound

Procedure

To a stirred solution of methyl 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetate (3.0 g, MW=435, 6.90 mmol) from Step 7 above in MeOH (25 mL) was added a solution of aqueous NaOH (6.9 mL of a 2.0 N solution, 13.8 mmol). The mixture was refluxed for 3 h and then cooled to ambient temperature. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and 0.25 M aqueous citric acid (75 mL). The organic phase was separated and washed with H2O (25 mL) and brine (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetic acid was obtained as an amorphous solid (HPLC retention time=9.4 min (method A)).