p-Toluenesulfonic acid → HCID 14969215, compound

HRID 1198043Notes

Reaction equation

HRID 1198043 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:36])[CH2:15][C:16](=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]C1CCCCO1)[CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C(Cl)(Cl)Cl>[CH3:12][CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[C:5]=1[NH:13][C:14](=[O:36])[CH2:15][C:16](=[O:35])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[CH3:11]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14969214HCID 14969214, compound

Product 1

HCID 14969215HCID 14969215, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N-[2,6-bis(1-methylethyl)phenyl)-3-oxo-14-[(tetrahydro-2H-pyran-2-yl)oxyltetradecanamide (0.97 g, 0.001 mol; see Example 6 for preparation) in 190 mL 95% MEOH, p-toluenesulfonic acid (0.055 g, 0.15 eq) was added and the reaction mixture was stirred for 16 hours at room temperature under a nitrogen atmosphere. The reaction mixture was then concentrated in vacuo (30° C.) to give a tacky residue. This residue was diluted with water and chloroform, the layers were separated and the aqueous layer was then extracted three times with chloroform. The combined organic layers were then washed two times with saturated NaCl solution, dried (MgSO4), and concentrated in vacuo to yield 0.63 g (0.001 mol, 79.4%) of the desired product.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo (30° C.)
  2. customto give a tacky residue
  3. customthe layers were separated
  4. extractionthe aqueous layer was then extracted three times with chloroform
  5. washThe combined organic layers were then washed two times with saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e434e7d10fdf4cc983db20cfd1e11221
Source dataset
uspto-grants-1994_01
Patent number
US05278326

Reaction notes

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