Trifluoroacetic acid → HCID 178511518, compound

HRID 1714390Notes

Reaction equation

HRID 1714390 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].C([O-])(O)=O.[Na+]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[F:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][C@H:11]3[CH2:12][CH2:13][C@H:8]([NH2:7])[CH2:9][CH2:10]3)[CH2:17][CH2:18]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178453905HCID 178453905, compound

Product 1

HCID 178511518HCID 178511518, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.155 g (0.368 mmol) of trans-(4-{2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-cyclohexyl)-carbamic acid tert-butyl ester was solved in dichloromethane (2 mL) and trifluoroacetic acid was added at 0° C. (0.230 mL, 3 mmol) and the mixture was stirred at room temperature overnight. NaHCO3 was slowly added until pH 9 and the mixture extracted 3 times with dichloromethane and ethyl acetate. The solvent was evaporated to yield 0.160 g (0.368 mmol, 100%) of a white solid that was used without purification on the next steps. MS (m/e): 321.4 (M+H+).

Workup

  1. extractionthe mixture extracted 3 times with dichloromethane and ethyl acetate
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ad611e1daab443358011df2d68aa551a
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

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