Tetrabutylammonium Fluoride → Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate

HRID 927924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 927924
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]>C1COCC1>[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][OH:39])=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2×

Produkt 1

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoateAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Tetrabutylammonium fluoride (1M solution in THF, 1.1 mL) was added to a stirred, cooled solution of methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (Intermediate 34, 0.43 g) in THF (10 mL) at 0° C. and the mixture was stirred at 0° C. for 40 minutes then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried (MgSO4) and filtered. 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 0-2% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (0.2 g) as a gum.

Aufarbeitung

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2%

Quellen und Nachweise

ORD-Eintrag
ord-a1a9d103046141fd823563acadee9fe4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290472B2

Notizen zur Reaktion

Wird geladen…