Triethylamine → HCID 59385205, compound

As shown in Reaction Scheme 10, 4′-nitro-1,1′-biphenyl-4-carboxylic acid (4.66 g, 19.2 mmol) was dissolved in methylene chloride (110 mL), and then oxalyl chloride (2.51 mL, 28.7 mmol) was added, followed by 3 drops of N,N-dimethylformamide. The resulting mixture was stirred at rt for 45 min, concentrated under reduced pressure, and further dried under vacuum for 30 min. The residue was dissolved in methylene chloride (75 mL) and added dropwise to an ice-cold mixture of methyl 2-methylalaninate hydrochloride (3.83 g, 24.9 mmol), methylene chloride (75 mL), and triethylamine (6.68 mL, 47.9 mmol). The resulting solution was stirred at rt for 1 h and then at 55° C. for 2 h. The mixture was allowed to cool to rt and was then washed with 1N aqueous HCl solution (5 mL) and water (2×20 mL). The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage® system, 4:1 hexanes/EtOAc) to afford methyl 2-methyl-N-[(4′-nitrobiphenyl-4-yl)carbonyl]alaninate (6.21 g, 95%). 1H NMR (400 MHz, CDCl3) δ 1.73 (s, 6H), 3.82 (s, 3H), 6.89 (broad s, 1H), 7.69 (d, 2H), 7.77 (d, 2H), 7.92 (d, 2H), 8.31 (d, 2H); LC-MS m/z 342.9 (MH+), retention time 2.98 minutes.

1. concentrationconcentrated under reduced pressure
2. customfurther dried under vacuum for 30 min
3. dissolutionThe residue was dissolved in methylene chloride (75 mL)
4. stirringThe resulting solution was stirred at rt for 1 h
5. waitat 55° C. for 2 h
6. temperatureto cool to rt
7. washwas then washed with 1N aqueous HCl solution (5 mL) and water (2×20 mL)
8. customThe organic layer was separated
9. dry with materialdried (MgSO4)
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography (Biotage® system, 4:1 hexanes/EtOAc)

ORD record

ord-8257f2db95a24bf78136b37f0f27ad10

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07759376B2