p-Toluenesulfonic acid monohydrate → HCID 86684758, compound

HRID 1408891Notes

Reaction equation

HRID 1408891 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C@@H:9]([OH:12])[CH2:10][OH:11])=[CH:4][C:3]=1[CH3:13].O.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1>COC(OC)(C)C>[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH2:8][C@@H:9]2[CH2:10][O:11][C:15]([CH3:20])([CH3:16])[O:12]2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86684756HCID 86684756, compound

Product 1

HCID 86684758HCID 86684758, compoundYield 970.4%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A suspension of 52 (3.2 g, 16.2 mmol) in dimethoxypropane (33 mL) was cooled with an ice bath and treated with paratoluene sulfonic acid monohydrate (0.31 g, 1.62 mmol). The ice bath was removed and the solution was stirred at room temperature for 16 hrs, cooled to 5° C. and treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to afford 3.80 g (97%) of 53 as an oil. 1HNMR (CDCl3) δ 1.34 (3 H, s), 1.41 (3 H, s), 2.37 (3 H, s), 2.81 (2 H, m), 3.61 (1 H, t, J=7.0 Hz), 4.03 (1 H, m, J=6.0 Hz), 4.27 (1 H, m, J=6.0 Hz), 7.44 (1 H, s), 8.10 (1 H, s). LC/MS (M+1) 258.

Workup

  1. temperaturewas cooled with an ice bath
  2. customThe ice bath was removed
  3. temperaturecooled to 5° C.
  4. additiontreated with saturated aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0e08543f62824590b3f2c3ee4e904dd7
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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