Hydrogen chloride-ethyl acetate → HCID 66906360, compound

HRID 1691734Notes

Reaction equation

HRID 1691734 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31]([OH:33])=[O:32])[CH2:24][CH:23]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:44].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:44].[F:43][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH:23]1[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31]([OH:33])=[O:32])[CH2:24]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66905989HCID 66905989, compound

Product 1

HCID 66906360HCID 66906360, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 161 mg of the crude 3-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(2-fluorophenyl)piperidin-1-yl]benzoic acid in 2.0 mL of ethyl acetate was added 1.00 mL of a 4 M hydrogen chloride/ethyl acetate solution at room temperature, followed by stirring for 1 hour. The solvent was removed by distillation under reduced pressure. The residue was purified by reverse phase silica gel column chromatography (acetonitrile-0.001 M hydrochloric acid) to obtain 58 mg of 3-[3-(2-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]benzoic acid hydrochloride as a white solid.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. customThe residue was purified by reverse phase silica gel column chromatography (acetonitrile-0.001 M hydrochloric acid)

Sources & evidence

ORD record
ord-40d79bdb2fdc432b994f30ac640dc2ca
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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