p-Toluenesulfonic acid → HCID 68008631, compound

HRID 1847124Notes

Reaction equation

HRID 1847124 reaction equation
COC[O:4][CH:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[CH:7]([C:8](=[O:32])[O:9][C:10]3[C@H:11]4[C@:23]([CH3:31])([CH2:24][CH2:25][C:26]=32)[C@@H:14]([C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]4)[CH2:6]1.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C)(C)C>[OH:4][C@@H:5]1[CH2:6][C@@H:7]2[C:8](=[O:32])[O:9][C:10]3[C@H:11]4[CH2:12][CH2:13][C@H:14]([C@@H:15]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21])[CH3:22])[C@@:23]4([CH3:31])[CH2:24][CH2:25][C:26]=3[C@@:27]2([CH3:30])[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 67610116HCID 67610116, compound

Product 1

HCID 68008631HCID 68008631, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Compound 56 (110 mg, 0.250 mmol) in obtained in Example 46 was dissolved in tert-butanol (5 mL), and pyrimidium p-toluenesulfonate (1.9 g; 7.4 mmol) was added thereto, followed by stirring at 80° C. for 1 hour. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by column chromatography to obtain the title compound (84 mg, 85%).

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto yield a residue
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e76571bd3de84392a7fa3eb746a38330
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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