p-Toluenesulfonic acid → HCID 12150670, compound

HRID 2086157Notes

Reaction equation

HRID 2086157 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)C(=N[NH:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([C:35](=[O:42])[N:36]([CH:38]3[CH2:41][CH2:40][CH2:39]3)[CH3:37])[CH:29]=2)=[C:22]([CH3:43])[CH:21]=1)C)C.C([O-])(O)=O.[Na+].[CH3:50][CH2:51][O:52][C:53]([CH3:55])=[O:54]>C1(C)C=CC=CC=1>[CH2:51]([O:52][C:53]([C:55]1[NH:19][C:20]2[C:21]([CH:1]=1)=[C:22]([CH3:43])[C:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([C:35](=[O:42])[N:36]([CH:38]3[CH2:41][CH2:40][CH2:39]3)[CH3:37])[CH:29]=1)=[C:24]([CH3:26])[CH:25]=2)=[O:54])[CH3:50]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86587765HCID 86587765, compound

Product 1

HCID 12150670HCID 12150670, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid (163 mg, 0.86 mmol) and 2-({4-[3-(Cyclobutyl-methyl-carbamoyl)-4-hydroxy-phenoxy]-3,5-dimethyl-phenyl}-hydrazono)-propionic acid ethyl ester (259 mg, 0.57 mmol) in toluene (2 mL) was heated to reflux. After vigorously stirring at reflux for 1 hour, the reaction mixture was then allowed to cool to room temperature. To which was added saturated aqueous NaHCO3 (15 mL) and EtOAc (20 mL). The EtOAc layer was separated, washed with saturated NaHCO3 (2 times 25 mL), brine (25 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (4% MeOH in CH2Cl2) to afford the title compound (136 mg) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ9.45 (s, 1H), 8.89 (br s, 1H), 7.23 (s, 1H), 7.16 (s, 1H), 7.04 (dd, 1H), 6.97 (d, 1H), 6.42 (d, 1H), 4.46-4.38 (m, 3H), 2.93 (s, 3H), 2.36 (s, 3H), 2.26 (s, 3H), 2.22-2.01 (m, 2H), 1.74-1.54 (m, 2H), 1.43 (t, 3H), 1.36-1.20 (m, 2H). MS (APCI+) Calc: 436.2, Found: 437.3 (M+1).

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux for 1 hour
  3. customThe EtOAc layer was separated
  4. washwashed with saturated NaHCO3 (2 times 25 mL), brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-25f8babaa8364a1794e173510ccc2e6c
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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