Isocyanate → HCID 68840252, compound

HRID 660538Notes

Reaction equation

HRID 660538 reaction equation
[N-]=C=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH2:36][C@@H:37]2[CH2:41][CH2:40][C:39](=[O:42])[NH:38]2)[CH:33]=[CH:32][C:31]=1[N:43]1[S:47](=[O:49])(=[O:48])[N:46](CC[Si](C)(C)C)[C:45](=[O:56])[CH2:44]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.O>[CH2:22]([O:29][C:30]1[CH:35]=[C:34]([CH2:36][C@@H:37]2[CH2:41][CH2:40][C:39](=[O:42])[NH:38]2)[CH:33]=[CH:32][C:31]=1[N:43]1[S:47](=[O:49])(=[O:48])[NH:46][C:45](=[O:56])[CH2:44]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 105034IsocyanateHCID 2724141Tetrabutylammonium Fluoride2×HCID 68838651HCID 68838651, compound

Product 1

HCID 68840252HCID 68840252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of PS-isocyanate resin (0.500 g) in THF is added TBAF (1M in THF, 2.5 mL) and the mixture is stirred at RT for 2 h. The resin is filtered off and the TBAF solution is added to a stirring solution of 5-[2-benzyloxy-4-((S)-5-oxopyrrolidin-2-ylmethyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (0.660 g, 1.28 mmol) in THF (20 mL). The mixture is stirred at 50° C. for 18 h. The mixture is allowed to cool to RT then is diluted with water and extracted with EtOAc (3×). The organic layer is washed with brine, dried over Na2SO4 and concentrated. The residue is purified on a reverse phase silica cartridge eluting with EtOH/H2O (10-60%) to provide the title compound: (M−1)−=414.

Workup

  1. filtrationThe resin is filtered off
  2. stirringThe mixture is stirred at 50° C. for 18 h
  3. temperatureto cool to RT
  4. extractionextracted with EtOAc (3×)
  5. washThe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified on a reverse phase silica cartridge
  9. washeluting with EtOH/H2O (10-60%)

Sources & evidence

ORD record
ord-138f5676d5504423861c5ad5320a86a6
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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