1,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester → Dimethyl 5-(3-((tert-butoxycarbonyl)(isobutyl)amino)propoxy)isophthalate
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CS(O[CH2:21][CH2:22][CH2:23][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])(=O)=O>CC#N>[C:32]([O:31][C:29]([N:24]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][CH2:22][CH2:21][O:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:30])([CH3:34])([CH3:35])[CH3:33]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dimethyl 5-hydroxyisophthalate (0.30 g, 1.44 mmol) cesium carbonate (0.95 g, 2.88 mmol) and CH3CN (25 mL) were stirred for 30 min. 3-((tert-Butoxycarbonyl)(isobutyl)amino)-propyl methanesulfonate (0.63 g, 2.02 mmol) was added and the reaction mixture was stirred for 16 h. The reaction mixture was concentrated under reduced pressure and partitioned between EtOAc (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product, which was used without further purification.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- custompartitioned between EtOAc (50 mL) and H2O (50 mL)
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (50 mL)
- dry with materialThe combined organics were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-58c5862b98c74117aeec2534017c1bf6
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09439433B2
Reaction notes
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