Acetonitrile → HCID 131733252, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([NH:12]C(OC(C)(C)C)=O)[CH2:7]1)[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.C(#N)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>>[F:36][C:37]([F:42])([F:41])[C:38]([O-:40])=[O:39].[Br-:21].[NH2:12][CH:8]1[CH2:9][CH2:10][CH2:11][N+:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH2:7]1.[NH2:12][CH:8]1[CH2:9][CH2:10][CH2:11][N+:6]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH2:7]1Participants
5
Procedure
To a solution of (3-tert-butoxycarbonylamino-piperidin-1-yl)-acetic acid ethyl ester (Intermediate 3.1.1, 800 mg, 2.3 mmol) and 1-(3-bromo-propyl)-4-methoxy-benzene (614 mg, 2.6 mmol) in acetonitrile (20 mL) K2CO3 (154 mg, 1.1 mmol) is added and the mixture heated at reflux with stirring for 72 hours. After removal of insolubles by filtration and evaporation of the solvent at reduced pressure the resulting material is dissolved in dry dichloromethane (6 mL) and trifluoroacetic acid (1 mL, 13 mmol) is added. After stirring of the resulting solution at room temperature for 4 hours volatiles are evaporated under reduced pressure and the resulting solid is co-evaporated several times with toluene. The material thus obtained is used as such in the next step. Yield: 0.58 g.