Diisopropylethylamine → (S)-Ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetate

HRID 391569

Reaktionsgleichung

Reaktionsgleichung von HRID 391569
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)C(C)C)(C)C.[C:20]1([S:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[NH:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([N:28]=[S@:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:27])=[O:9])[CH:5]=[N:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 887075-Bromonicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 76585231ethyl(S-phenylsulfonimidoyl)acetate

Produkt 1

HCID 57657890(S)-Ethyl {N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}acetateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-bromonicotinic acid (343 mg, 1.66 mmol) in anhydrous DMF (5.5 mL) was added N,N-diisopropylethylamine (0.58 mL, 3.32 mmol) and ethyl (S-phenylsulfonimidoyl)acetate (415 mg, 1.83 mmol) followed by the final addition of (benzotriazol-1-yloxy)-tris(dimethylamino)-phosphonium hexafluorophophate (0.81 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 20 min, and then partitioned between saturated aqueous NaHCO3 and EtOAc. The organic layer was separated and washed once with brine and dried over anhydrous Na2SO4. The organic layer was concentrated and the residue purified by chromatography (silica gel, gradient elution (5:1 Hexane/EtOAc to 3:1 Hexane/EtOAc). The product containing fractions were concentrated to give the title compound as a white solid (230 mg, 34%).

Aufarbeitung

  1. custompartitioned between saturated aqueous NaHCO3 and EtOAc
  2. customThe organic layer was separated
  3. washwashed once with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated
  6. customthe residue purified by chromatography (
  7. washsilica gel, gradient elution (5:1 Hexane/EtOAc to 3:1 Hexane/EtOAc)
  8. additionThe product containing fractions
  9. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-68b7fcc21d90467e8caebe1e8bf2c4a4
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383825B2

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