1,1'-Carbonyldiimidazole → (S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester

To a solution of 2-amino-4-methoxy-benzoic acid (1.0 g, 5.98 mmol) and 1,1′-carbonyldiimidazole (980 mg, 6.04 mmol) in pyridine (5 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.9 mL, 6.02 mmol). The mixture is stirred at room temperature for 2 hours follows by the addition of (S)-2-amino-hexanoic acid methyl ester hydrochloride (1.1 g, 6.06 mmol). The reaction mixture is stirred at room temperature for 16 hours and diluted with EtOAc (100 mL), the solution is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, and is concentrated. The resulting residue is purified by flash chromatography with 60% EtOAc in hexanes as the eluent to afford (S)-2-(2-amino-4-methoxy-benzoylamino)-hexanoic acid methyl ester (1.03 g, 59%).

1. stirringThe reaction mixture is stirred at room temperature for 16 hours
2. washthe solution is washed with H2O (50 mL×3)
3. dry with materialThe organic layer is dried over sodium sulfate
4. concentrationis concentrated
5. customThe resulting residue is purified by flash chromatography with 60% EtOAc in hexanes as the eluent

ORD record

ord-8bfc118369f54071991b23aa6fcb154a

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08377949B2