Trifluoroacetic acid → HCID 68196376, compound

HRID 1626812Notes

Reaction equation

HRID 1626812 reaction equation
[CH2:1]([O:3][C:4](=[O:46])[CH2:5][NH:6][C:7]([C:9]1[C:14]([O:15]CC2C=CC=CC=2)=[C:13]([CH3:23])[N:12]=[C:11]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][C:40]([CH2:43][OH:44])=[CH:39][CH:38]=4)=[C:33]([Cl:45])[CH:32]=3)[CH2:27][CH2:26]2)[N:10]=1)=[O:8])[CH3:2].[F:47][C:48]([F:53])([F:52])[C:49](O)=[O:50].C(=O)([O-])O.[Na+]>ClCCl>[Cl:45][C:33]1[CH:32]=[C:31]([N:28]2[CH2:29][CH2:30][CH:25]([CH2:24][C:11]3[N:10]=[C:9]([C:7]([NH:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:46])=[O:8])[C:14]([OH:15])=[C:13]([CH3:23])[N:12]=3)[CH2:26][CH2:27]2)[CH:36]=[CH:35][C:34]=1[C:37]1[CH:42]=[CH:41][C:40]([CH2:43][O:44][C:49](=[O:50])[C:48]([F:53])([F:52])[F:47])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68196375HCID 68196375, compound

Product 1

HCID 68196376HCID 68196376, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl({[5-(benzyloxy)-2-({1-[2-chloro-4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidin-4-yl]carbonyl}amino)acetate (0.96 g, 1.5 mmol) was dissolved in dichloromethane (20 mL), and trifluoroacetic acid (20 mL) was added under a nitrogen atmosphere, followed by stirring at room temperature for 7 hours. An aqueous sodium hydrogencarbonate solution was added to the reaction solution for neutralization, followed by extraction with dichloromethane, and subsequently the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate), and a fraction corresponding to the Rf value=0.80 (dichloromethane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.74 g, 1.3 mmol) as a yellow oil (yield 90%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. concentrationsubsequently the organic layer was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.80 (dichloromethane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f80510ef1ad3467b926a620c7334425e
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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