Isocyanate → 4-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile

HRID 660758Notes

Reaction equation

HRID 660758 reaction equation
[N-]=C=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([CH2:50][C:51]([CH3:56])([CH3:55])[CH2:52][C:53]#[N:54])[CH:33]=[CH:34][C:35]=1[N:36]1[CH2:40][C:39](=[O:41])[N:38](CC[Si](C)(C)C)[S:37]1(=[O:49])=[O:48])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.Cl>[CH2:22]([O:29][C:30]1[CH:31]=[C:32]([CH2:50][C:51]([CH3:56])([CH3:55])[CH2:52][C:53]#[N:54])[CH:33]=[CH:34][C:35]=1[N:36]1[CH2:40][C:39](=[O:41])[NH:38][S:37]1(=[O:49])=[O:48])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium Fluoride2×HCID 689223464-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-3,3-dimethylbutyronitrile

Product 1

HCID 688387924-[3-Benzyloxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-3,3-dimethylbutyronitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of PS-isocyanate resin (100 mg) in THF is added TBAF (1M in THF, 0.5 mL) and the mixture is stirred at RT for 2 h. The resin is filtered off and the TBAF solution is added to a solution of 4-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-3,3-dimethylbutyronitrile (25 mg, 0.047 mmol) in THF (5 mL). The mixture is stirred at RT for 18 h then is diluted with 1N HCl and extracted with EtOAc. The organic layer is washed with brine, dried over Na2SO4 and concentrated to give the title compound which is used directly in the next step.

Workup

  1. filtrationThe resin is filtered off
  2. stirringThe mixture is stirred at RT for 18 h
  3. extractionextracted with EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-00d5f24d438b4339b6b0e59801a83851
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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