Sodium Bicarbonate → HCID 70183466, compound

HRID 1289041Notes

Reaction equation

HRID 1289041 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][CH2:7][N:8]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)=[C:12]([CH2:24][CH3:25])[C:11](=[O:26])[NH:10][C:9]1=[O:27])=[O:4].O.[C:29]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:2][C:3]([CH:5]=[CH:6][CH2:7][N:8]1[C:13]([C:14](=[O:23])[C:15]2[CH:16]=[C:17]([CH3:22])[CH:18]=[C:19]([CH3:21])[CH:20]=2)=[C:12]([CH2:24][CH3:25])[C:11](=[O:26])[NH:10][C:9]1=[O:27])=[O:4])[CH3:29]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70183042HCID 70183042, compound

Product 1

HCID 70183466HCID 70183466, compoundYield 148.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 100 mg (0.27 mmol) of the compound obtained from Example 8 in 10 ml of anhydrous ethanol was added 20 mg of p-toluenesulfonic acid monohydrate. The reaction mixture was refluxed with stirring for about 48 hours, neutralized with sodium bicarbonate, and evaporated under reduced pressure to give a light brown residue, which was purified by flash chromatography using a mixture of ethyl acetate and hexane (1:2) as an eluent to afford 60 mg (yield 58%) of the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customevaporated under reduced pressure
  3. customto give a light brown residue, which
  4. customwas purified by flash chromatography
  5. additiona mixture of ethyl acetate and hexane (1:2) as an eluent

Sources & evidence

ORD record
ord-406e3619338845f78afce1ecc850ecfd
Source dataset
uspto-grants-1998_05
Patent number
US05747500

Reaction notes

Loading…