Methanol → 3-[[5-(3-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acid

HRID 1427100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427100
[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:31])=[C:14]([CH:30]=2)[C:15]([NH:17][C:18]2[C:19]([CH3:29])=[C:20]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:21]([O:23]C)=[O:22])=[O:16])[CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:31])=[C:14]([CH:30]=2)[C:15]([NH:17][C:18]2[C:19]([CH3:29])=[C:20]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:21]([OH:23])=[O:22])=[O:16])[CH2:5]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707331Methyl 3-[[5-(3-hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Produkt 1

HCID 867073323-[[5-(3-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acidAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of aqueous 4N NaOH (2.00 ml) is added to a stirred solution of methyl 3-[[5-(3-hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.3 g, 0.75 mmol) in THF:MeOH (5 ml:2 ml). After 3 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with 1N HCl, and extracted with 10% IPA in CH2Cl2. The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with diethyl ether and filtered to afford the title compound as an off-white solid (0.274 g, 94%). Mass spectrum (m/z): 383.2 (M+1).

Aufarbeitung

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with 10% IPA in CH2Cl2
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with diethyl ether
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-f872883745744520ac46439bd177cc81
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933098B2

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