p-Toluenesulfonic acid → HCID 178441215, compound

HRID 2360287Notes

Reaction equation

HRID 2360287 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:24][C:25]([CH3:27])=[CH2:26])([CH2:15][CH2:16][O:17]C2CCCCO2)[C:12](=[O:14])[N:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH2:16][OH:17])([CH2:24][C:25]([CH3:27])=[CH2:26])[C:12](=[O:14])[N:13]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178441184HCID 178441184, compound

Product 1

HCID 178441215HCID 178441215, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-methylallyl)-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)thiazol-4(5H)-one (420 mg, 1.07 mmol) and p-toluenesulfonic acid (100 mg) in MeOH (5.0 mL) was stirred for 16 h at room temperature. The reaction mixture was then concentrated in vacuo, and sat'd NaH2PO4 was added. The mixture was then extracted with EtOAc, and the organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as solid. MS (ES+): 309 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionwas added
  3. extractionThe mixture was then extracted with EtOAc
  4. washthe organic layer was washed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (4:1; Hexane:EtOAc)

Sources & evidence

ORD record
ord-938021aa2bd0449ab41351d2027c8cba
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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