Chlorotrimethylsilane → HCID 68838651, compound

HRID 660537Notes

Reaction equation

HRID 660537 reaction equation
BrCCBr.C[Si](Cl)(C)C.I[CH2:11][C@H:12]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:40]([O:47][C:48]1[CH:53]=[C:52](I)[CH:51]=[CH:50][C:49]=1[N:55]1[S:59](=[O:61])(=[O:60])[N:58]([CH2:62][CH2:63][Si:64]([CH3:67])([CH3:66])[CH3:65])[C:57](=[O:68])[CH2:56]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C.O.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:40]([O:47][C:48]1[CH:53]=[C:52]([CH2:11][C@@H:12]2[CH2:13][CH2:14][C:15](=[O:17])[NH:16]2)[CH:51]=[CH:50][C:49]=1[N:55]1[S:59](=[O:60])(=[O:61])[N:58]([CH2:62][CH2:63][Si:64]([CH3:66])([CH3:65])[CH3:67])[C:57](=[O:68])[CH2:56]1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

10

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 80271Tri-o-tolylphosphineHCID 10977129HCID 10977129, compoundHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 68838651HCID 68838651, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

Zinc dust (0.69 g, 10.66 mmol) is placed in a round bottom flask and heated under vacuum to remove traces of water. After cooling, DMF (3 mL) is added, followed by 1,2-dibromoethane (0.061 mL, 0.708 mmol). The solution is heated until effervescence occurs, then cooled under N2. To the solution is added TMSCl (0.135 mL, 1.06 mmol). A solution of (S)-5-iodomethylpyrrolidin-2-one (0.40 g, 1.78 mmol) in DMF (5 mL) is added to the mixture and stirred until TLC indicates the absence of starting material. Pd2(dba)3 (0.043 g, 0.047 mmol) and tri-o-tolylphosphine (0.11 g, 0.365 mmol) are added, followed by the dropwise addition of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (0.645 g, 1.18 mmol) in DMF (10 mL). The mixture is stirred at RT for 4 h, then heated to 45° C. and stirred for 18 h. The mixture is allowed to cool to RT and diluted with water. A yellow precipitate forms after the addition of water. The precipitate is filtered, washed with water and dried under reduced pressure to afford the title compound: (M+H)+=516.

Workup

  1. temperatureheated under vacuum
  2. customto remove traces of water
  3. temperatureAfter cooling
  4. additionDMF (3 mL) is added
  5. temperatureThe solution is heated until effervescence
  6. temperaturecooled under N2
  7. stirringThe mixture is stirred at RT for 4 h
  8. stirringstirred for 18 h
  9. temperatureto cool to RT
  10. filtrationThe precipitate is filtered
  11. washwashed with water
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-a6cc4dd0057a40ae8399d27511d0b20c
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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