Diisopropylethylamine → HCID 86603035, compound

A solution of 2.1 g of 4,4,4-trifluoro-3-trifluoromethyl-butyric acid (10 mmol) in 80 ml DMF was treated with 3.12 g of TBTU (10 mmol) and 8.55 ml of N,N-diisopropylethyl amine and stirred for 5 min at rt under argon. Then 1.93 ml of 4-tert-butylbenzylamine (11 mmol) were added and the reaction mixture was stirred 17 h at rt. The reaction mixture was then diluted with 400 ml water and extracted twice with EtOAc, the combined organic phases washed with brine, dried over magnesium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 4:1) to give 2.14 g of N-(4-tert-butyl-benzyl)-4,4,4-trifluoro-3-trifluoromethyl-butyramide as a light yellow solid (60%).

1. stirringthe reaction mixture was stirred 17 h at rt
2. extractionextracted twice with EtOAc
3. washthe combined organic phases washed with brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 4:1)

ORD record

ord-d9492f96ec1a40c09a11f21639f6e7ae

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2