Lithium Hydroxide → 1369142-11-9
Reaction equation
[CH:1]1([C:4]2[CH:8]=[CH:7][N:6](S(C3C=CC=CC=3)(=O)=O)[C:5]=2[C:18]([O:20]C)=[O:19])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.O>[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:18]([OH:20])=[O:19])[CH2:2][CH2:3]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of the starting methyl 3-cyclopropyl-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (0.9 g, 3 mmol) in tetrahydrofurane (4.6 mL) and water (2.3 mL) was added lithium hydroxide (0.29 g, 12 mmol) and this mixture was heated to 100° C. in a microwave vial during 4 hours. Next, the reaction mixture was poured into water (50 mL) and this aqueous phase was washed with diethyl ether (2×). Afterwards, the aqueous layer was acidified until pH=3 by adding solid phosphoric acid and extracted with ethyl acetate (3×). The organic solution was washed with water and brine, dried (Na2SO4) and concentrated in vacuum to give 370 mg of the title compound.
Workup
- washthis aqueous phase was washed with diethyl ether (2×)
- additionby adding solid phosphoric acid
- extractionextracted with ethyl acetate (3×)
- washThe organic solution was washed with water and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-b29118530622441c803f73d15e999b80
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340547B2
Reaction notes
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