p-Toluenesulfonic acid → HCID 67609817, compound
Reaction equation
COC[O:4][C@@H:5]1[CH2:28][C@@H:9]2[C:10](=[O:27])[O:11][C:12]3[C@@H:13]4[CH2:20][CH2:19][C@H:18]([C@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[C@@:14]4([CH3:26])[CH2:15][CH2:16][C:17]=3[C@@:8]2([CH3:29])[CH2:7][CH2:6]1.CC1C=CC(S(O)(=O)=O)=CC=1.[Cl-].[NH4+]>C(O)(C)(C)C>[OH:4][C@@H:5]1[CH2:28][C@@H:9]2[C:10](=[O:27])[O:11][C:12]3[C@@H:13]4[CH2:20][CH2:19][C@H:18]([C@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[C@@:14]4([CH3:26])[CH2:15][CH2:16][C:17]=3[C@@:8]2([CH3:29])[CH2:7][CH2:6]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
Compound 67 (581.6 mg, 1.431 mmol) obtained in Example 63 was dissolved in tert-butanol (48 mL), and pyrimidium p-toluenesulfonate (3.6 g; 14 mmol) was added thereto, followed by stirring at 105° C. for 4 hours. The reaction mixture was cooled to 0° C., a saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate (50 mL×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to yield a residue. The residue was purified by silica gel column chromatography, followed by purification by high-speed liquid chromatography (60 to 100% acetonitrile/water) to obtain the title compound (150 mg, 29%).
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- extractionfollowed by extraction with ethyl acetate (50 mL×3)
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customto yield a residue
- customThe residue was purified by silica gel column chromatography
- customfollowed by purification by high-speed liquid chromatography (60 to 100% acetonitrile/water)
Sources & evidence
- ORD record
- ord-9239e60779b14a98a97fb602a85691fb
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952003B2
Reaction notes
Loading…