CN1CCOCC1.[ClH:8].CN(C)CCCN=C=NCC.C(OC(NCC(N[C@@H]1CN(C(OC(C)(C)C)=O)[C@@H](C(O)=O)C1)=O)=O)(C)(C)C.[Cl:47][C:48]1[CH:49]=[C:50]([CH:58]=[C:59]([Cl:61])[CH:60]=1)[O:51][CH:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1.ON1C2C=CC=CC=2N=N1>O1CCCC1.CN(C)C=O>[ClH:47].[ClH:8].[Cl:47][C:48]1[CH:49]=[C:50]([CH:58]=[C:59]([Cl:61])[CH:60]=1)[O:51][CH:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1N-Methylmorpholine (70 μL) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (114 mg) were added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-D-proline (Compound D105 (F), 220 mg), 4-(3,5-dichlorophenoxy)piperidine (154 mg) and 1-hydroxybenzotriazole (85 mg) in tetrahydrofuran (8 mL) and N,N-dimethylformamide (2 mL) at room temperature. After stirring at room temperature for 12 hr, the reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with saturated sodium hydrogen carbonate and brine. After drying over anhydrous sodium sulfate, the organic layer was evaporated in vacuo. The residue was washed with hexane to give the titled compound (347 mg) as a white powder.
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