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Methanol → 3-[[3-(4-Hydroxy-1-piperidyl)naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoic acid

HRID 239989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 239989
[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[C:12]([C:20]([NH:22][C:23]3[C:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:26]([O:28]C)=[O:27])=[O:21])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:6][CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[C:12]([C:20]([NH:22][C:23]3[C:24]([CH3:34])=[C:25]([CH:30]=[CH:31][C:32]=3[CH3:33])[C:26]([OH:28])=[O:27])=[O:21])[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH2:9]1
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Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707373Methyl 3-[[3-(4-hydroxy-1-piperidyl)naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate

Produkt 1

HCID 867073743-[[3-(4-Hydroxy-1-piperidyl)naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoic acidAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of aqueous 2N NaOH (3.00 ml) is added to a stirred solution of methyl 3-(3-(4-hydroxypiperidin-1-yl)-1-naphthamido)-2,4-dimethylbenzoate (0.10 g, 0.23 mmol) in THF:MeOH (3 ml:1 ml). After 12 hours at room temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with aqueous 1N HCl and extracted with dichloromethane (2×20 ml). 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 a white solid (0.028 g, 29%). Mass spectrum (m/z): 419.2 (M+1).

Aufarbeitung

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with dichloromethane (2×20 ml)
  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-3f8fd9d0fe3f42fdae07a67413c5d416
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642768B2

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