Isocyanate → HCID 68839001, compound

HRID 660504Notes

Reaction equation

HRID 660504 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N-]=C=O.[CH2:22]([O:29][C:30]1[CH:35]=[C:34](/[CH:36]=[CH:37]/[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:33]=[CH:32][C:31]=1[N:45]1[S:49](=[O:51])(=[O:50])[N:48](CC[Si](C)(C)C)[C:47](=[O:58])[CH2:46]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:22]([O:29][C:30]1[CH:35]=[C:34](/[CH:36]=[CH:37]/[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:33]=[CH:32][C:31]=1[N:45]1[S:49](=[O:51])(=[O:50])[NH:48][C:47](=[O:58])[CH2:46]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium FluorideHCID 68839387HCID 68839387, compound

Product 1

HCID 68839001HCID 68839001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (1.0M in THF, 2 mL) is added to a solution of PS-isocyanate resin (0.5 g) in THF (2 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-((E)-3-phenylpropenyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (89 mg, 0.163 mmol) in THF (1 mL). The reaction is stirred at 75° C. for 1 h then the mixture is cooled and concentrated. The residue is partitioned between EtOAc and water and the organic layer is washed with 2N HCl (3×) and brine. The organic layer is dried over sodium sulfate and the solvent removed under reduced pressure to afford the title compound as a light yellow foam: (M−1)−=433.

Workup

  1. filtrationThe resin is filtered off
  2. stirringThe reaction is stirred at 75° C. for 1 h
  3. temperaturethe mixture is cooled
  4. concentrationconcentrated
  5. customThe residue is partitioned between EtOAc and water
  6. washthe organic layer is washed with 2N HCl (3×) and brine
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d6a893671b964c8e8ec87126ee0a061b
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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