Citric Acid → HCID 23157506, compound

HRID 508052Notes

Reaction equation

HRID 508052 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]2[CH:38]=[CH:37][C:20]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[C:25]([F:36])[CH:24]=3)=[CH:19][CH:18]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:7]([CH2:16][C:17]2[CH:38]=[CH:37][C:20]([CH2:21][NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[C:25]([F:36])[CH:24]=3)=[CH:19][CH:18]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157204HCID 23157204, compound

Product 1

HCID 23157506HCID 23157506, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-[4-({4-[(3-tert-butyl-5-phenyl-1H-pyrazol-1-yl)methyl]benzyl}amino)-2-fluorophenyl]propanoate (150 mg, 0.29 mmol) in ethanol (5 mL) and tetrahydrofuran (5 mL) was added 1 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the mixture was weakly acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give the title compound (91 mg, yield 65%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b97805acbc0e404f9a7bfa70bdf043c3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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