p-Toluenesulfonic acid → HCID 67315532, compound

HRID 2059900Notes

Reaction equation

HRID 2059900 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.CO[CH:14](OC)[CH2:15][NH:16][C:17](=[O:41])[C@@H:18]([NH:27][S:28]([C:31]1[C:36]([CH3:37])=[CH:35][C:34]([O:38][CH3:39])=[CH:33][C:32]=1[CH3:40])(=[O:30])=[O:29])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>O1CCOCC1>[CH3:39][O:38][C:34]1[CH:35]=[C:36]([CH3:37])[C:31]([S:28]([N:27]2[CH:14]=[CH:15][NH:16][C:17](=[O:41])[C@@H:18]2[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=[O:30])=[O:29])=[C:32]([CH3:40])[CH:33]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67316034HCID 67316034, compound

Product 1

HCID 67315532HCID 67315532, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

PTSA (0.62 eq) was added to a solution of (S)-tert-butyl 4-(2,2-dimethoxyethylamino)-3-(4-methoxy-2,6-dimethylphenylsulfonamido)-4-oxobutanoate (1.26 mmol) in dioxane (12 ml) and the mixture was stirred for 16 h at room temperature. The solvent was removed under vacuum and the residue taken up in ethyl acetate. The organic phase was extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated to small volume under vacuum. The crude product was processed by column chromatography. Yield: 35%

Workup

  1. customThe solvent was removed under vacuum
  2. extractionThe organic phase was extracted with water and saturated sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-d6b1f865062742698d4d6eebbb7f2786
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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