Hydrochloric Acid → HCID 86657657, compound

HRID 217475Notes

Reaction equation

HRID 217475 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][C@@H:34]([CH3:39])[C:35]([F:38])([F:37])[F:36])[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([O:27]CC)=[O:26])[CH2:20]3)[CH2:14][O:15]2)=[CH:10][CH:9]=1.[OH-].[Na+].[ClH:44].Cl.O1CCOCC1>CCO.O1CCOCC1.C1COCC1>[ClH:44].[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][C@@H:34]([CH3:39])[C:35]([F:36])([F:37])[F:38])[CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([OH:27])=[O:26])[CH2:20]3)[CH2:14][O:15]2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 204431481,4-Dioxane hydrochlorideHCID 86657658HCID 86657658, compound

Product 1

HCID 86657657HCID 86657657, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl (3R)-1-[(7-{[3-(trifluoromethyl)-4-{[(2S)-1,1,1-trifluoropropan-2-yl]oxy}benzyl]oxy}-2H-chromen-3-yl)methyl]piperidine-3-carboxylate (271 mg) in EtOH (5.4 mL)-THF (2.7 mL) was added a 1 M aqueous NaOH solution (923 μL), followed by stirring at 50° C. for 2 hours. The reaction liquid was cooled to room temperature, then 1 M hydrochloric acid (923 μL) was added thereto, and the vehicle was evaporated. The residue was purified by reverse phase chromatography (H2O:MeCN=100:0 to 30:70) to obtain a yellow oily substance, which was dissolved in dioxane (3 mL), treated with 4 N HCl/dioxane (1 mL), and washed with IPE to obtain (3R)-1-[(7-{[3-(trifluoromethyl)-4-{[(2S)-1,1,1-trifluoropropan-2-yl]oxy}benzyl]oxy}-2H-chromen-3-yl)methyl]piperidine-3-carboxylic acid hydrochloride (215 mg) as a white powder.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customthe vehicle was evaporated
  4. customThe residue was purified by reverse phase chromatography (H2O:MeCN=100:0 to 30:70)
  5. customto obtain a yellow oily substance, which
  6. washwashed with IPE

Sources & evidence

ORD record
ord-7988428c74e243a28dc9e6cb9efa191c
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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