Hydrochloric Acid → 2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoic acid
Reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10]([O:12]C)=[O:11])=[N:3]1.[OH-].[Na+].O1CCCC1.Cl>CO>[CH3:1][N:2]1[C:6]([S:7][CH3:8])=[CH:5][C:4]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10]([OH:12])=[O:11])=[N:3]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of methyl 2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate (2.52 g), 2N aqueous sodium hydroxide solution (6.3 ml), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 50° C. for 3 hr. To the reaction mixture was added 1N hydrochloric acid (13 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (2.47 g, quantitatively) as a colorless oil from the fraction eluted with ethyl acetate. MS: 285 (MH+).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-189967406106439f89fc9e77c55cd973
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349886B2
Reaction notes
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