p-Toluenesulfonic acid monohydrate → HCID 86684755, compound

HRID 1408888Notes

Reaction equation

HRID 1408888 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[F: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]([F: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 86684754HCID 86684754, compound

Product 1

HCID 86684755HCID 86684755, compoundYield 967.5%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A suspension of 3 (2.50 g, 12.2 mmol) in dimethoxypropane (25 mL) was cooled with an ice bath and treated with paratoluene sulfonic acid monohydrate (0.23 g, 1.22 mmol). The ice bath was removed and the solution was stirred at room temperature for 16 hrs, cooled to 5° C. and treated with aqueous sat. NaHCO3 and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated to afford 2.90 g of 31 (97%) as an oil. 1HNMR (CDCl3) δ 1.34 (3 H, s), 1.42 (3 H, s), 2.87 (2 H, d, J=6.0 Hz), 3.62 (1 H, t, J=7.0 Hz), 4.08 (1 H, t, J=6.0 Hz), 4.30 (1 H, q, J=6.0 Hz), 7.46 (1 H, d, J=9.0 Hz), 8.12 (1 H, s). LC/MS (M+1) 247.

Workup

  1. temperaturewas cooled with an ice bath
  2. customThe ice bath was removed
  3. temperaturecooled to 5° C.
  4. additiontreated with aqueous sat. NaHCO3
  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-94b9dbd7b6c040998c4efd226af43938
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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