Ethanol → HCID 59331501, compound
Reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]([O:28]CC)=[O:27])=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)C.[OH-].[Na+]>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of ethyl 5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrole-2-carboxylate (1.5 g) in a mixed solvent of ethanol (15 mL) and tetrahydrofuran (15 ml) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 70° C. for 3 hr. After cooling to room temperature, the reaction mixture was concentrated, the residue was diluted with ethyl acetate, and 1N hydrochloric acid (10 mL) was added. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.3 g, yield 93%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. MS: 404 (MH+).
Workup
- temperatureAfter cooling to room temperature
- concentrationthe reaction mixture was concentrated
- additionthe residue was diluted with ethyl acetate, and 1N hydrochloric acid (10 mL)
- additionwas added
- 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-48b9d6a8cdec4b2a9311d2a22938d964
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318746B2
Reaction notes
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