Triethylamine → HCID 68837979, compound

HRID 660592Notes

Reaction equation

HRID 660592 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:18](=[O:29])[CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:33])[CH:31]=[CH2:32].C(N(CC)CC)C>C(#N)C>[C:35]([O:34][C:30](=[O:33])/[CH:31]=[CH:32]/[C:13]1[CH:12]=[CH:11][C:10]([N:16]2[CH2:17][C:18](=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:20]2(=[O:22])=[O:21])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68837979HCID 68837979, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(2-benzyloxy-4-iodo-phenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (544 mg, 1 mmol), t-butyl acrylate (154 mg, 1.2 mmol) and triethylamine (1.01 g, 10 mmol) in 5 mL of acetonitrile is added Pd (OAc)2 (10 mg). The mixture is heated at 100° C. for 18 h. After allowing to cool to RT the solvent is removed under reduced pressure and the residual oil purified by flash chromatography using methylene chloride to elute the title compound as an oil.

Workup

  1. temperatureto cool to RT the solvent
  2. customis removed under reduced pressure
  3. customthe residual oil purified by flash chromatography
  4. washto elute the title compound as an oil

Sources & evidence

ORD record
ord-5754d5a90d0f42ae93b6629302604f35
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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