Isocyanate → 5-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660477

Reaction equation

HRID 660477 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N-]=C=O.[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([I:36])[CH:33]=[CH:32][C:31]=1[N:37]1[S:41](=[O:43])(=[O:42])[N:40](CC[Si](C)(C)C)[C:39](=[O:50])[CH2:38]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]([I:36])[CH:33]=[CH:32][C:31]=1[N:37]1[S:41](=[O:43])(=[O:42])[NH:40][C:39](=[O:50])[CH2:38]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium FluorideHCID 667569375-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrabutylammonium fluoride (1.0M in THF, 15 mL) is added to a solution of PS-isocyanate resin (3.5 g) in THF. 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-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (5.0 g, 9.18 mmol) in THF. The reaction is stirred at 50° C. for 18 h. The mixture is cooled and concentrated. The residue is partitioned between EtOAc and water and the organic layer is washed with 1N HCl (5×50 mL) and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by reverse phase chromatography using a 10-60% gradient of EtOH/water as eluent to afford the title compound as a light yellow solid: (M−1)−=442.

Workup

  1. filtrationThe resin is filtered off
  2. stirringThe reaction is stirred at 50° C. for 18 h
  3. temperatureThe mixture is cooled
  4. concentrationconcentrated
  5. customThe residue is partitioned between EtOAc and water
  6. washthe organic layer is washed with 1N HCl (5×50 mL) and brine
  7. dry with materialThe organic layer is dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue is purified by reverse phase chromatography

Sources & evidence

ORD record
ord-a83f45cde89f4f848cb5f96f5240b938
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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