Potassium Carbonate → (2s)-2-[[5-Chloro-4'-[[(1-ethylpropyl)amino]carbonyl]-3'-fluoro[1,1'-biphenyl]-2-yl]oxy]-propanoic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:15])=[C:10]([F:22])[CH:9]=2)[CH:7]=1.CC1C=CC(O[C@H:30]([CH3:35])[C:31]([O:33]C)=[O:32])=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][C@@H:30]([CH3:35])[C:31]([OH:33])=[O:32])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:15])=[C:10]([F:22])[CH:9]=2)[CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
The product of step c) (300 mg), the product of step d) (219 mg) and potassium carbonate (135 mg) in acetonitrile (10 ml) were charged to a flask and stirred at 50° C. for 16 h. The reaction mixture was cooled, diluted with water (20 ml) and extracted with diethyl ether (3×10 ml). The organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting yellow oil was dissolved in a 1:1 mixture of THF/methanol (10 ml) and 1M NaOH added (1.1 ml). The mixture was stirred at room temperature for 4 h and then concentrated in vacuo. The residue was purified by RPHPLC to give the title compound as a white solid (175 mg).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with diethyl ether (3×10 ml)
- washThe organic fractions were washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- dissolutionThe resulting yellow oil was dissolved in a 1:1 mixture of THF/methanol (10 ml) and 1M NaOH
- additionadded (1.1 ml)
- stirringThe mixture was stirred at room temperature for 4 h
- concentrationconcentrated in vacuo
- customThe residue was purified by RPHPLC
Sources & evidence
- ORD record
- ord-ee20e342a18c4bef809c243428ae7db4
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737135B2
Reaction notes
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