Lithium Hydroxide → (R)-3-(2-Chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

LiOH (173 mg, 4.156 mmol, 2 eq), dissolved in water (12 ml), was added dropwise to an ice-cooled (0° C.) solution of (R)-methyl 3-(2-chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-29) (0.8 g, 2.078 mmol, 1 eq) in MeOH:THF (1:1, 24 ml), and stirring was carried out for 8 h at RT. After monitoring by thin-layer chromatography, the reaction solution was concentrated and the residue was taken up in water (30 ml) and extracted with ethyl acetate (25 ml). The aqueous phase was adjusted to pH 3 with 2 M HCl and extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. Yield: 78% (600 mg, 1.62 mmol).

1. concentrationthe reaction solution was concentrated
2. extractionextracted with ethyl acetate (25 ml)
3. extractionextracted with ethyl acetate (2×50 ml)
4. washThe combined organic phases were washed with sat. NaCl solution (50 ml)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-4600169c7cef469dae6df57acae665f3

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680159B2