p-Toluenesulfonic acid → HCID 53984281, compound

HRID 1602643Notes

Reaction equation

HRID 1602643 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C@H:8]([CH2:18][CH2:19][C:20]2([CH3:25])OCC[O:21]2)[C:7]1=[O:26])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C@H:8]([CH2:18][CH2:19][C:20](=[O:21])[CH3:25])[C:7]1=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 53774644HCID 53774644, compound

Product 1

HCID 53984281HCID 53984281, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 12-4 (260 mg, 0.6925 mmol), p-TSA (10 mg) and acetone (20 mL) was heated at reflux for 1 hr. NaHCO3 was added to the cooled reaction mixture and then the mixture was concentrated. The residue was diluted with CHCl3 and then washed with brine, dried (MgSO4), and concentrated to afford 12-5 as an oil.

Workup

  1. temperatureat reflux for 1 hr
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with CHCl3
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d455e2410ac341f4acf6a11a795040c5
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

Loading…