p-Toluenesulfonic acid → HCID 10437193, compound

HRID 2120914Notes

Reaction equation

HRID 2120914 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:27])=[O:26])=[CH:19][CH:20]=4)[C:15](=[N:36][NH:37]C(OC(C)(C)C)=O)[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[N:36](=[C:15]1[C:14]2[CH:13]=[C:12]([S:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)(=[O:10])=[O:11])[CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][C:18]([S:25]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=1)(=[O:27])=[O:26])=[CH:19][CH:20]=2)[NH2:37]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12093194HCID 12093194, compound

Product 1

HCID 10437193HCID 10437193, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 4A (218 mg, 0.34 mmol) in absolute ethanol was treated with three crystals of p-toluenesulfonic acid and heated at reflux. After 3 hours, the mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (85% ethyl acetate/hexanes) to provide the title compound as a yellow solid (36 mg, 20% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.41 (d, 2H), 8.78 (bs, 2H), 8.63 (bs, 1H), 8.28 (d, 1H), 8.02-8.1 (m, 2H), 7.81 (dd, 1H), 7.70 (dd, 1H), 6.91-7.01 (m, 2H), 6.49-6.61 (m, 4H), 6.33-6.42 (m, 2H); MS (ESI) 535 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. concentrationwas concentrated under reduced pressure
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (85% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9f539d8985004c7b90ceafb663312b72
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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