Reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:7]([C:12]([OH:14])=O)[C:8]2=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:28]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.O>ClCCl>[CH:28]1([NH:34][C:12]([C:7]2[C:8](=[O:11])[C:9]3[C:5]([C:6]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=[C:2]([OH:1])[CH:10]=3)=[O:14])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1Participants
Procedure
6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid (100 mg, 0.38 mmol) obtained in Step 2 was dissolved in dichloromethane, and triethylamine (175 μl, 1.25 mmol) and cyclohexylamine (43 μl, 0.38 mmol) were added thereto at 10° C. Then, bis(2-oxo-3-oxazoline)phosphoryl chloride (100 mg, 0.38 mmol) was further added thereto, stirred for 10˜20 minutes at RT, and then stirred for additional 1 hr in a water bath. After water was added to complete the reaction, the mixture washed with sodium bicarbonate and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4, concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 26 mg of the titled compound (yield: 20.0%) as a red solid.
Workup
- customat 10° C
- stirringstirred for additional 1 hr in a water bath
- customthe reaction
- washthe mixture washed with sodium bicarbonate
- extractionextracted with dichloromethane
- customThe organic layer was separated
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated under a reduced pressure
- customThe resulting residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-41523592252d464e85fe5b4db700fe11
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745439B2
Linked notes
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