Hydrochloric Acid → 4-[[4-[[4-(2,2,2-Trifluoroethoxy)-1,2-benzoxazol-3-yl]oxymethyl]piperidin-1-yl]methyl]oxane-4-carboxylic acid

HRID 714571Notes

Reaction equation

HRID 714571 reaction equation
[F:1][C:2]([F:34])([F:33])[CH2:3][O:4][C:5]1[C:10]2[C:11]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][C:23]4([C:29]([O:31]C)=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH2:18][CH2:17]3)=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl>O1CCCC1.CO.[OH-].[Na+]>[F:34][C:2]([F:1])([F:33])[CH2:3][O:4][C:5]1[C:10]2[C:11]([O:14][CH2:15][CH:16]3[CH2:17][CH2:18][N:19]([CH2:22][C:23]4([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH2:20][CH2:21]3)=[N:12][O:13][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 69317159HCID 69317159, compound

Product 1

HCID 119977224-[[4-[[4-(2,2,2-Trifluoroethoxy)-1,2-benzoxazol-3-yl]oxymethyl]piperidin-1-yl]methyl]oxane-4-carboxylic acidYield 58.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 4-{[4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidin-1-yl]methyl}-tetrahydro-2H-pyran-4-carboxylate (89 mg, 0.18 mmol, PCT WO2006090224 EXAMPLE 1, Step 5) in tetrahydrofuran (1 mL), methanol (1 mL) and 2 N aq. sodium hydroxide (1 mL) is stirred at 70° C. for 17 h. The mixture is neutralized with 2 N hydrochloric acid (1 mL) and formed precipitate is filtered. The precipitate is triturated with diethylether to give 50 mg (58%) of the title compound as a white solid.

Workup

  1. customformed precipitate
  2. filtrationis filtered
  3. customThe precipitate is triturated with diethylether

Sources & evidence

ORD record
ord-cb9e918f549d4365a6530158553a1d92
Source dataset
uspto-grants-2015_11
Patent number
US09187463B2

Reaction notes

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