Pyridine → HCID 50898472, compound

HRID 1847122Notes

Reaction equation

[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:4]([C:5](=[O:29])[O:6][C:7]3[C@H:8]4[C@:20]([CH3:28])([CH2:21][CH2:22][C:23]=32)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]4)[CH2:3]1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](Cl)=[O:36].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35]([O:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:4]([C:5](=[O:29])[O:6][C:7]3[C@H:8]4[C@:20]([CH3:28])([CH2:21][CH2:22][C:23]=32)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]4)[CH2:3]1)=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 2 (51 mg, 0.13 mmol) obtained in Example 2 was dissolved in dichloromethane (0.65 mL), and furan-2-carboxylic acid chloride (0.025 mL, 0.26 mmol) and pyridine (0.041 mL, 0.51 mmol) were added thereto, followed by stirring at 0° C. for 3 hours. 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. A residue obtained by concentrating the organic layer under reduced pressure was purified by preparative thin layer chromatography to obtain the title compound (65 mg, 100%).

Workup

extractionfollowed by extraction with ethyl acetate twice
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customA residue obtained
concentrationby concentrating the organic layer under reduced pressure
customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-308314a7d0b74110899f40f96dd693a3
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952003B2

Reaction notes

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