Diisopropylethylamine → HCID 59619453, Verbindung

To a mixture of (1R,2R,4S)-4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (150 mg, 0.29 mmol), N,N-diisopropylethylamine (0.15 mL, 0.87 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (221 mg, 0.58 mmol) in acetonitrile was added 1-amino-cyclopropyl cyanic hydrochloride (41 mg, 0.34 mmol). The reaction mixture was stirred at room temperature for 16 h then concentrated in vacuo and partitioned between ethyl acetate and an aqueous solution of sodium carbonate (5% w/w). The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with aqueous hydrochloric acid (1N) and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichloromethane/methanol (98:2 v/v) as eluant to afford the title compound (144 mg, 85%) as a brown solid. MS (EI): 584.0 (M−H)−.

1. concentrationthen concentrated in vacuo
2. custompartitioned between ethyl acetate
3. extractionThe aqueous layer was extracted with ethyl acetate
4. washthe combined organic layers were washed with aqueous hydrochloric acid (1N) and brine
5. dry with materialthen dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography on silica gel with a gradient of dichloromethane/methanol (98:2 v/v) as eluant

ORD-Eintrag

ord-709e4a2601904c6bb3ed54a1625e74b0

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07893099B2