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 2056769Notes

Reaction equation

HRID 2056769 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9ab89c240cd4963a54d2dd0534597bd
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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