Isocyanate → HCID 68839776, compound

HRID 660726Notes

Reaction equation

HRID 660726 reaction equation
[N-]=C=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([C:36]2[S:40][CH:39]=[N:38][CH:37]=2)[CH:33]=[CH:32][C:31]=1[N:41]1[S:45](=[O:47])(=[O:46])[N:44](CC[Si](C)(C)C)[C:43](=[O:54])[CH2:42]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.CCOC(C)=O>[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([C:36]2[S:40][CH:39]=[N:38][CH:37]=2)[CH:33]=[CH:32][C:31]=1[N:41]1[S:45](=[O:47])(=[O:46])[NH:44][C:43](=[O:54])[CH2:42]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium FluorideHCID 68843203HCID 68843203, compound

Product 1

HCID 68839776HCID 68839776, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of PS-isocyanate resin (2.0 g) in THF (5 mL) is added tetrabutylammonium fluoride (1.0 M in THF, 2.17 mL) and the mixture is stirred at RT for 2 h. The resin is filtered off and the filtrate is added to a solution of 5-(2-benzyloxy-4-thiazol-5-yl-phenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (272 mg, 0.543 mmol) in THF (1 mL) and the mixture is stirred at 50° C. for 18 h. The reaction mixture is cooled and diluted with EtOAc, washed with 1N HCl and dried over MgSO4. The solvent is removed under reduced pressure and the residue is purified by column chromatography eluting with MeOH/EtOAc to afford the title compound as a yellow solid: (M+1)+=402.

Workup

  1. filtrationThe resin is filtered off
  2. stirringthe mixture is stirred at 50° C. for 18 h
  3. temperatureThe reaction mixture is cooled
  4. washwashed with 1N HCl
  5. dry with materialdried over MgSO4
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is purified by column chromatography
  8. washeluting with MeOH/EtOAc

Sources & evidence

ORD record
ord-cc1102983419491e88183ea5a1be592f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…