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

HRID 1193288Notes

Reaction equation

HRID 1193288 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[C:6]([N:8]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]>O.CO.C1COCC1>[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[C:6]([N:8]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66799128(R)-Methyl 3-(2-chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 66798968(R)-3-(2-Chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4600169c7cef469dae6df57acae665f3
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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