Ethyl Acetate → HCID 68867039, compound

HRID 660587Notes

Reaction equation

HRID 660587 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[N:26]1[CH2:30][C:29](=[O:31])[N:28](CC[Si](C)(C)C)[S:27]1(=[O:39])=[O:38])[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][C:20](=[O:22])[CH3:21])[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:23]=[CH:24][C:25]=1[N:26]1[CH2:30][C:29](=[O:31])[NH:28][S:27]1(=[O:39])=[O:38])[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][C:20](=[O:22])[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 68842039HCID 68842039, compound

Product 1

HCID 68867039HCID 68867039, 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)-acetamide (76 mg, 0.133 mmol) in DMF (3 mL) is added CsF (81 mg, 0.533 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 removed under reduced pressure to give the title compound which is used directly in the next step.

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 removed under reduced pressure

Sources & evidence

ORD record
ord-866c06c202fc4d9582c8c5a22c9fba74
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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