Diisopropyl Ether → 4-({4-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-4-oxobutanoyl}amino)benzoic acid hydrochloride

HRID 1691711Notes

Reaction equation

HRID 1691711 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28](=[O:43])[CH2:29][CH2:30][C:31]([NH:33][C:34]2[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=2)=[O:32])[CH2:24][CH:23]1[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[CH:45]=1)[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:51].C(OCC)(=O)C.C(OC(C)C)(C)C>C(OCC)(=O)C>[ClH:51].[F:50][C:46]1[CH:45]=[C:44]([CH:23]2[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH2:27][CH2:26][N:25]([C:28](=[O:43])[CH2:29][CH2:30][C:31]([NH:33][C:34]3[CH:42]=[CH:41][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=3)=[O:32])[CH2:24]2)[CH:49]=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 21866389Hydrogen chloride-ethyl acetateHCID 669061274-({4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-4-oxobutanoyl}amino)benzoic acid

Product 1

HCID 669057984-({4-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-4-oxobutanoyl}amino)benzoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 107 mg of 4-({4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-4-oxobutanoyl}amino)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 2 hours. Diisopropylether was added thereto, and the resulting precipitate was collected by filtration, and dried under reduced pressure to obtain 28 mg of 4-({4-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-4-oxobutanoyl}amino)benzoic acid hydrochloride as a pale yellow solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-186fc3580ad8436c8af52f9449158975
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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