Reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=O)[CH3:13].[N:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[F:34])=[N+:26]=[N-:27].O>CN(C=O)C>[CH:19]1([C:17]2[N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:26]=[N:27][C:16]=2[C:15]([O:14][CH2:12][CH3:13])=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20]1Participants
Procedure
DBU (2.99 ml; 20.06 mmol; 1.10 eq.) was dissolved in DMF (25 ml) and put under nitrogen atmosphere. 3-Cyclopentyl-3-oxo-propionic acid ethyl ester (Pharmacore, 3.695 g; 20.06 mmol; 1.10 eq.) was added to the mixture and it was stirred for 15 min. Then a solution of 1-azido-2-fluorobenzene, prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945, (2.5 g; 18.23 mmol; 1 eq.) in DMF (5 mL) was added dropwise to the solution at room temperature. The mixture was stirred at 90° C. for 2 hours. Water (50 mL) was added to the cooled reaction mixture and the aqueous layer was extracted with EtOAc (3×50 mL). Combined organics were washed with water and brine, dried over MgSO4 and concentrated under vacuum affording the title compound as a yellow oil. It was used in the next step without further purification. LC/MS (Method B): 304.2 (M+H)+.
Workup
- stirringThe mixture was stirred at 90° C. for 2 hours
- extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
- washCombined organics were washed with water and brine
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-1265a8aa4ec24b1c82bdda4769ce40cf
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202856B2
Linked notes
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