Cesium fluoride → {(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic Acid Tert-butyl Ester

HRID 660525Notes

Reaction equation

HRID 660525 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]([CH3:40])([CH3:39])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][C:20](=[O:22])[N:19](CC[Si](C)(C)C)[S:18]2(=[O:30])=[O:29])=[C:13]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[F-].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]([CH3:40])([CH3:39])/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][C:20](=[O:22])[NH:19][S:18]2(=[O:30])=[O:29])=[C:13]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 68839103((E)-3-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-1,1-dimethylallyl)-carbamic Acid Tert-butyl Ester

Product 1

HCID 68843602{(E)-3-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-1,1-dimethylallyl}-carbamic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ((E)-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-1,1-dimethylallyl)-carbamic acid tert-butyl ester (150 mg, 0.2 mmol) in DMF (3 mL) is added CsF (83 mg, 0.53 mmol) and the mixture is stirred at 60° C. for 3 h. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using 10-20% MeOH/EtOAc as eluent to give the title compound as a solid.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-66c86c995063465499f61f1d99514f5d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…