Trifluoroacetic acid → HCID 66865450, compound

HRID 222575Notes

Reaction equation

HRID 222575 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:33][CH:34]=3)=[CH:25][CH:24]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[CH3:38][S:35]([N:32]1[CH2:31][CH:30]=[C:29]([C:26]2[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)=[CH:24][CH:25]=2)[CH2:34][CH2:33]1)(=[O:36])=[O:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 668646881-Piperidinecarboxylic acid, 4-[[4-[1,2,3,6-tetrahydro-1-(methylsulfonyl)-4-pyridinyl]phenoxy]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 66865450HCID 66865450, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

Trifluoroacetic acid (2.98 g, 1.97 mL, 26.10 mmol) is added to a solution of 4-[4-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenoxymethyl]-piperidine-1-carboxylic acid tert-butyl ester (1.20 g, 2.61 mmol) in dichloromethane (13 mL). The mixture is stirred at 23° C. for 30 min. 2 M aq. sodium hydroxide is added. The resulting white precipitate is filtered and washed with water. The mother liquor is extracted with dichloromethane. The combined organic layers are dried over anhydrous sodium sulfate, filtered, and the solvent is removed to obtain a white solid which is combined with the initial precipitate and dried under high vacuum for 16 h. Diethyl ether is added and the solid is filtered and washed with ethyl acetate to obtain 0.810 g of an off-white solid. MS (m/z) 351 (M+1).

Workup

  1. filtrationThe resulting white precipitate is filtered
  2. washwashed with water
  3. extractionThe mother liquor is extracted with dichloromethane
  4. dry with materialThe combined organic layers are dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. customto obtain a white solid which
  8. customdried under high vacuum for 16 h
  9. additionDiethyl ether is added
  10. filtrationthe solid is filtered
  11. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5c024ea63cd54bffab2429acb24fa1ae
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Reaction notes

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