Potassium Carbonate → (3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

HRID 1159595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1159595
[CH3:1][C:2]1([CH3:15])[O:11][C:10]2[C:5](=[CH:6][C:7]([C:12]#[N:13])=[CH:8][CH:9]=2)[C@@H:4]2[O:14][C@H:3]12.[NH:16]1[CH:20]=[CH:19][NH:18][C:17]1=[S:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:14][C@@H:3]1[C@H:4]([S:21][CH:17]2[N:18]=[CH:19][CH:20]=[N:16]2)[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:12]#[N:13])[CH:6]=2)[O:11][C:2]1([CH3:15])[CH3:1]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12013862-MercaptoimidazoleHCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

Produkt 1

HCID 68644174(3S,4R)-3-Hydroxy-4-(2H-imidazol-2-ylsulfanyl)-2,2-dimethyl-chroman-6-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(S,S)-2,2-Dimethyl-1a,7b-dihydro-2H-1,3-dioxa-cyclopropa[a]naphthalene-6-carbonitrile (1 mmoL), 1,3-dihydro-imidazole-2-thione (1 mmoL) and anhydrous K2CO3 (1.5 mmoL) in DMF (5 mL) were heated at 100° C. for 4˜6 hrs. The solid was filtered off and the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated NH4Cl, brine, then dried over anhydrous Na2SO4, filtered and concentrated to yield a yellow oil. Silica gel chromatography separation yielded the title compound as a white solid.

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated NH4Cl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow oil
  8. customSilica gel chromatography separation

Quellen und Nachweise

ORD-Eintrag
ord-9305f411534b41ee978505cf1fe25b0b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812183B2

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