Sodium hydride → 2-[(1S)-1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]isothiazolidine 1,1-dioxide

HRID 2056769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056769
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]1[C:16]2[CH:17]=[CH:18][C:19]([NH:21][S:22]([CH2:25][CH2:26][CH2:27]Cl)(=[O:24])=[O:23])=[CH:20][C:15]=2[CH2:14][CH2:13][O:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+]>CN(C=O)C>[Si:1]([O:8][CH2:9][CH2:10][C@H:11]1[C:16]2[CH:17]=[CH:18][C:19]([N:21]3[CH2:27][CH2:26][CH2:25][S:22]3(=[O:24])=[O:23])=[CH:20][C:15]=2[CH2:14][CH2:13][O:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 69307817N-[(1S)-1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]-3-chloro-1-propanesulfonamide

Produkt 1

HCID 693065112-[(1S)-1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]isothiazolidine 1,1-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of N-[(1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]-3-chloro-1-propanesulfonamide (0.367 g, 0.82 mmol) in DMF (8 mL), cooled to 0° C., was added sodium hydride (60% dispersion in oil) (0.036 g, 0.9 mmol) and the mixture allowed to warm to room temperature. After 30 min, the reaction was quenched by addition of water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The title compound, as an oil, was used in the next step without further purification.

Aufarbeitung

  1. customthe reaction was quenched by addition of water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe title compound, as an oil, was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d9ab89c240cd4963a54d2dd0534597bd
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335660B2

Notizen zur Reaktion

Wird geladen…