Dimethylamine → HCID 19073175, compound

Temperature

20 °C

To a stirred 4° C. CH2Cl2 solution (5 mL) containing HNMe2 (180 mg, 4 mmol) under N2, was added 2M AlMe3 in toluene (2 mL, 4 mmol). The reaction was warmed to 20° C. and stirred for five minutes before adding a CH2Cl2 solution (4 mL) containing α-[[(trifluoroacetyl)amino]methyl]benzeneacetic acid, ethyl ester (600 mg, 2.1 mmol). After two days, the reaction was quenched with 1 N aq. HCl, and extracted 3× with EtOAc. The EtOAc fractions were washed with brine, dried over Na2SO4, and concentrated. The crude product was chromatographed on silica gel using 4:1 hexane/EtOAc to elute 380 mg (63%) of the desired trifluoroacetamide which was heated to 60° C. for five hours in MeOH (2 mL) containing 1N aq. NaOH (3 mL). The reaction was diluted with brine, extracted 4× with EtOAc, dried over Na2SO4, and concentrated to yield the title compound as a clear oil (280 mg, 74%).

1. customTo a stirred 4° C
2. waitAfter two days
3. customthe reaction was quenched with 1 N aq. HCl
4. extractionextracted 3× with EtOAc
5. washThe EtOAc fractions were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe crude product was chromatographed on silica gel using 4:1 hexane/EtOAc
9. washto elute 380 mg (63%) of the desired trifluoroacetamide which
10. temperaturewas heated to 60° C. for five hours in MeOH (2 mL)
11. additioncontaining 1N aq. NaOH (3 mL)
12. additionThe reaction was diluted with brine
13. extractionextracted 4× with EtOAc
14. dry with materialdried over Na2SO4
15. concentrationconcentrated

ORD record

ord-2c750ec486f24cf8a3f150c84a55f198

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05776983