4-Formylbenzoic acid → 3-(4-Formylbenzoylamino)propionic acid ethyl ester
Reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].ON1C2C=CC=CC=2N=N1.Cl.[CH2:23]([O:25][C:26](=[O:30])[CH2:27][CH2:28][NH2:29])[CH3:24].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:23]([O:25][C:26](=[O:30])[CH2:27][CH2:28][NH:29][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=1)[CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-formylbenzoic acid (27.4 g, 0.18 mol) in DMF (300 mL) was added N-ethyl-N′-3-dimethylaminopropylcarbodiimide (34.5 g, 0.18 mol) and N-hydroxybenzotriazole (29.9 g, 0.22 mol). The resulting mixture was stirred at room temperature for 1 hour, then β-alanine ethyl ester hydrochloride (65.4 g, 0.42 mol) and diisopropylethylamine (76 mL, 0.44 mol) was added. After 16 hours stirring at ambient temperature the reaction mixture was partitioned between water (600 mL) and ethyl acetate (600 mL). The organic phase was washed successively with hydrochloric acid (1N, 300 mL), saturated aqueous ammonium chloride (300 mL), water (2×300 mL) and brine (300 mL). The solvent was removed by rotary evaporation to leave an oil, which crystallised upon standing to afford 29.0 g (65%) of 3-(4-formylbenzoylamino)propionic acid ethyl ester.
Workup
- stirringAfter 16 hours stirring at ambient temperature the reaction mixture
- customwas partitioned between water (600 mL) and ethyl acetate (600 mL)
- washThe organic phase was washed successively with hydrochloric acid (1N, 300 mL), saturated aqueous ammonium chloride (300 mL), water (2×300 mL) and brine (300 mL)
- customThe solvent was removed by rotary evaporation
- customto leave an oil, which
- customcrystallised
Sources & evidence
- ORD record
- ord-268a591b22bb4f82ba10844e3f2f9260
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875760B2
Reaction notes
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