Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate → methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate

HRID 927923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927923
[C:1]([NH:4][C:5]1[C:14]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[H][H]>O1CCOCC1.C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([NH:4][C:5]1[C:14]([C@H:15]2[CH2:19][CH2:18][O:17][C@H:16]2[CH2:20][OH:21])=[CH:13][CH:12]=[C:11]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 70983847methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoateAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (Intermediate 38, 0.2 g) in dioxane (4 mL) and acetic acid (1 mL) was treated under an atmosphere of nitrogen with palladium hydroxide on carbon (10%, 0.03 g). The nitrogen was replaced by hydrogen and the mixture was stirred under an atmosphere of hydrogen overnight. The mixture was filtered through Celite and the pad was washed thoroughly with ethyl acetate. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-[cis-(2RS,3RS)-2-(hydroxymethyl)tetrahydrofuran-3-yl]benzoate (0.14 g) as a white solid.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washthe pad was washed thoroughly with ethyl acetate
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

Quellen und Nachweise

ORD-Eintrag
ord-4ab099e12fdc4939a777b4c08bdd6a57
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

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