Pyridine → HCID 72550214, Verbindung

HRID 1774439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774439
[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[N:45]1C=CC=CC=1.C(=O)(O)[O-].[NH4+]>CS(C)=O.O>[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:45])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 60155116HCID 60155116, Verbindung

Produkt 1

HCID 72550214HCID 72550214, VerbindungAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoic acid (100 mg, 0.26 mmol) in DMSO (5 mL) was added Boc anhydride (69 mg, 0.31 mmol) followed by pyridine (24 mg, 0.26 mmol) and stirred at room temperature for 5 min. Ammonium bicarbonate (62 mg, 0.78 mmol) was added and stirred for additional 1 h. Reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (25 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by CombiFlash using 20% ethyl acetate in chloroform as an eluent to yield 59 mg (59%) of the title compound as an off white solid.

Aufarbeitung

  1. stirringstirred for additional 1 h
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe organic layer was washed with brine (25 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by CombiFlash

Quellen und Nachweise

ORD-Eintrag
ord-158bfbe895e54617a069ac760a1b63aa
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260376B2

Notizen zur Reaktion

Wird geladen…