Lithium hydroxide, monohydrate → (R)-3-(2-tert-Butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1193287Notes

Reaction equation

HRID 1193287 reaction equation
O[Li].O.[C:4]([C:8]1[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=1[C:10]([NH:12][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)=[O:11])([CH3:7])([CH3:6])[CH3:5].OS([O-])(=O)=O.[K+]>O.CO.C1COCC1>[C:4]([C:8]1[CH:29]=[CH:28][CH:27]=[CH:26][C:9]=1[C:10]([NH:12][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)=[O:11])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 66798706(R)-Methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 66798589(R)-3-(2-tert-Butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH.H2O (700 g, 17.0 mmol, 6 eq), dissolved in water (30 ml), was added dropwise to a cooled (0° C.) solution of (R)-methyl 3-(2-tert-butylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-27) (1.0 g, 2.8 mmol, 1 eq) in MeOH:THF (1:1, 60 ml), and stirring was carried out for 4 h at RT. After monitoring by thin-layer chromatography, the reaction solution was reduced under reduced pressure and the residue was taken up in water (50 ml), acidified with KHSO4 solution and extracted with dichloromethane (2×100 ml). The combined organic phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated and dried under reduced pressure. Yield: 900 mg

Workup

  1. additionwas added dropwise to
  2. extractionextracted with dichloromethane (2×100 ml)
  3. washThe combined organic phases were washed with sat. NaCl solution (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-410a35576ba7456785f4e43500c651e0
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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