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

HRID 1193291
Notes
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Reaction equation

HRID 1193291 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66798976(R)-Methyl 3-(2-methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 66798553(R)-3-(2-Methylpropylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

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

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextracted with dichloromethane (2×80 ml)
  3. washThe combined organic phases were washed with sat. NaCl solution (40 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb8b4f7cb71344fa91a2f560e58ba37c
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680159B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes