Lithium tri-s-butylborohydride → 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

HRID 1698190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698190
[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:13]\[S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>C1COCC1>[CH3:1][S:2]([C:5]1[S:6][C:7]([C@@H:10]([NH:13][S:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:3])=[O:4]

Komponenten

4

Edukt 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 87126692(NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

Produkt 1

HCID 667274522-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in THF (5 mL) was added a 1 M solution of lithium tri-sec-butylborohydride (L-Selectride) (0.58 mL, 0.58 mmol) in THF dropwise. After 2.5 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL), and the aqueous layer was separated. The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL)
  2. customthe aqueous layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6f780b8560a04be8a4e2a4ac4818cd55
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163918B2

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