Ethyl p-methylbenzenesulfonate → HCID 21345202, compound

HRID 367094Notes

Reaction equation

HRID 367094 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=1.[OH-].[K+].[C:23]1(C)C=CC(S(OCC)(=O)=O)=C[CH:24]=1>CN(C)C=O>[CH2:23]([O:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:5]=[N:6][CH:7]=1)[CH3:24]

Participants

5

Reactant 3

HCID 6638Ethyl p-methylbenzenesulfonateHCID 14797Potassium HydroxideHCID 21345207HCID 21345207, compound

Product 1

HCID 21345202HCID 21345202, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-hydroxy-3-(1-Boc-2-(S)-azetidinylmethoxy)pyridine (500 mg, 1.78 mmol, from step 120f) in dimethylformamide (15 mL) was treated with ground KOH (170 mg, 1.7 mmol) and stirred for 30 minutes at room temperature. To this mixture was rapidly added ethyl p-toluenesulfonate (430 mg, 2.14 mmol), and the resultant was stirred at 80° C. overnight. The mixture was concentrated to remove the dimethylformamide, and the residue was diluted with water and extracted with EtOAc. The organic extracts were combined, dried (MgSO4), filtered and concentrated under vacuum to give 1.0 g of unpurified product. This material was purified by chromatography (silica gel: hexane/EtOAc, 1:1) to give 537 mg (98%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ: 1.40 (s, 9H), 1.42 (t, J=6 Hz, 3H), 2.30 (m, 2H), 3.92 (t, J=9 Hz, 2H), 4.05 (q, J=6 Hz, 2H), 4.30 (m, 1H), 4.54 (m, 1H), 6.80 (m, 1H), 7.95 (m, 2H). MS (CI/NH3) m/e: 309 (M+H)+.

Workup

  1. stirringthe resultant was stirred at 80° C. overnight
  2. concentrationThe mixture was concentrated
  3. customto remove the dimethylformamide
  4. additionthe residue was diluted with water
  5. extractionextracted with EtOAc
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give 1.0 g of unpurified product
  10. customThis material was purified by chromatography (silica gel: hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-b4a9c91bb5254ecd9db147734cb8aa36
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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