p-Toluenesulfonic acid → HCID 178441215, compound

HRID 1158099

Reaction equation

HRID 1158099 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-86df10609ede45059fd061a2edc5bfcf
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Linked notes

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