(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one synthesis

8synthesis methods

Product Name:(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one
CAS Number:781650-41-7
Molecular formula:C14H15F5N2O
Molecular Weight:322.27

Acetamide, N-[6-(2,3-difluorophenyl)-2,3,4,7-tetrahydro-2-oxo-1-(2,2,2-trifluoroethyl)-1H-azepin-3-yl]-

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(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one

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Yield:781650-41-7 80%

Reaction Conditions:

Stage #1: N-[6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)-2,3,4,7-tetrahydro-1H-azepin-3-yl]acetamidewith hydrogenchloride in 1,4-dioxane;water at 85; for 12 h;
Stage #2: with sodium hydroxide in 1,4-dioxane;tert-butyl methyl ether;water; pH=8 - 10;

Steps:

7.6.1; 2

To a 288 mL dioxane solution of the Step 5 compound (36 g, 99.4 mmol) was added 6 equiv of 3N HCL. The solution was heated at 85° C. for 12 hours. After cooling, the solution was diluted with 230 mL MTBE added and the pH adjusted to 8-10 with 10N NaOH followed by 1N NaOH. After the phase cut, the aqueous was extracted with 230 mL MTBE and the combined organic layer washed with 390 mL 15% NaCl and assayed for product (25.4 g, 79.3 mmol, 80% assay yield).

References:

US2009/124799,2009,A1 Location in patent:Page/Page column 4; 13

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References