[NH2:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8].[F:9][C:10]([F:16])([F:15])[CH2:11][C:12](O)=[O:13].OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[F:9][C:10]([F:16])([F:15])[CH2:11][C:12]([NH:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8])=[O:13](±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one (128 mg, 1.13 mmol) was mixed with 3,3,3-trifluoropropionic acid in 2.3 mL of N,N-dimethylformamide. Hydroxybenzotriazole (17.4 mg, 0.11 mmol) was added followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol). The pH of the reaction mixture was adjusted to 8.5 with triethylamine and the mixture was allowed to stir at ambient temperature for 2 hours. Water was then added and the reaction mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, then dried (sodium sulfate) and concentrated to give the crude product. This was purified by silica gel chromatography to afford 120 mg (45%) of 3,3,3-trifluoro-N-[(±)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide.
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