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

HRID 1193287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193287
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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-410a35576ba7456785f4e43500c651e0
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680159B2

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