Ethyl Acetate → HCID 68995192, compound

HRID 660673Notes

Reaction equation

HRID 660673 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[N:27]1[CH2:31][C:30](=[O:32])[N:29](CC[Si](C)(C)C)[S:28]1(=[O:40])=[O:39])[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][C:26]=1[N:27]1[CH2:31][C:30](=[O:32])[NH:29][S:28]1(=[O:39])=[O:40])[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][S:20]([CH3:23])(=[O:21])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 68999551HCID 68999551, compound

Product 1

HCID 68995192HCID 68995192, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-((1R*,2S*)-2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzyl}-cyclohexyl)-methanesulfonamide (118 mg, 0.194 mmol) in DMF (3 mL) is added CsF (118 mg, 0.78 mmol) and the mixture is stirred at 90° C. for 1 h. Ethyl acetate is added and the mixture is washed with 1N HCl and brine. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure to give the title compound.

Workup

  1. washthe mixture is washed with 1N HCl and brine
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-dd9e53d8b26541958c61412d7494c87c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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