Lithium hydroxide, monohydrate → (R)-3-(2-Methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylic acid
Reaction equation
O[Li].O.[CH3:4][CH:5]([CH3:24])[CH2:6][S:7]([NH:10][C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]C)=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)(=[O:9])=[O:8]>O.CO.C1COCC1>[CH3:4][CH:5]([CH3:24])[CH2:6][S:7]([NH:10][C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)(=[O:8])=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
LiOH.H2O (200 mg, 4.8 mmol, 3 eq) in water (3 ml) was added dropwise to a cooled (0° C.) solution of (R)-methyl 3-(2-methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate (C-03) (500 mg, 1.6 mmol, 1 eq) in MeOH:THF (1:1, 12 ml), and stirring was carried out for 6 h at RT. After monitoring by thin-layer chromatography, the reaction solution was concentrated under reduced pressure and the residue was taken up in water (50 ml), adjusted to pH 2 with 2M HCl solution and extracted with dichloromethane (2×80 ml). The combined organic phases were washed with sat. NaCl solution (40 ml), dried over sodium sulfate and concentrated and dried under reduced pressure. Yield: 450 mg
Workup
- concentrationthe reaction solution was concentrated under reduced pressure
- extractionextracted with dichloromethane (2×80 ml)
- washThe combined organic phases were washed with sat. NaCl solution (40 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-bb8b4f7cb71344fa91a2f560e58ba37c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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