Reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:4][C:3]=2[O:2]1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=1>C1COCC1.CCOCC>[O:9]1[C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][C:12]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=3)=[O:14])=[CH:4][C:3]=2[O:2][CH2:1]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-(3,4-methylenedioxyphenyl)-propionic acid (501 mg, 2.58 mmol) in anhydrous THF (10 mL) were added N-methylmorpholine (0.28 mL, 2.58 mmol) and isobutylchloroformate (0.33 mL, 2.58 mmol) at 0° C. After 30 min, at 0° C., a solution of methyl 4-aminobenzoate (390 mg, 2.58 mmol) in anhydrous THF (2 mL) was added to the reaction mixture. After 30 min the temperature was allowed to warm up to rt and stir for 24 hrs. After extraction with EtOAc (100 mL), washing with HCl (0.1 N, 50 mL) and a saturated aqueous solution of NaHCO3 (50 mL), the organic layer was dried over sodium sulfate and evaporated under vacuo to give a solid. The residue was taken up in Et2O, filtrated and washed with Et2O gave the title compound as a white solid (62%) in 99.4% purity by HPLC (MaxPlot detection between 230 and 400 nm).
Workup
- waitAfter 30 min the temperature was allowed
- extractionAfter extraction with EtOAc (100 mL)
- washwashing with HCl (0.1 N, 50 mL)
- dry with materiala saturated aqueous solution of NaHCO3 (50 mL), the organic layer was dried over sodium sulfate
- customevaporated under vacuo
- customto give a solid
- filtrationfiltrated
- washwashed with Et2O
Sources & evidence
- ORD record
- ord-022d783b1f5d4d81be1e8acae2189d65
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696231B2
Linked notes
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