Tetrahydrofuran → HCID 57889099, compound

Reaction equation

[CH:1]1([N:6]=[C:7]=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:10][C@H:11]([CH:30]([CH3:32])[CH3:31])[C:12]([N:14]1[CH2:19][CH2:18][C@@:17]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)([OH:20])[C:16]([CH3:29])([CH3:28])[CH2:15]1)=[O:13].C1COCC1>C(N(CC)CC)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C@@:17]2([OH:20])[CH2:18][CH2:19][N:14]([C:12](=[O:13])[C@H:11]([NH:10][C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])[CH:30]([CH3:32])[CH3:31])[CH2:15][C:16]2([CH3:28])[CH3:29])=[CH:26][CH:25]=1

Participants

Procedure

A reaction tube was charged with cyclopentyl isocyanate (9 μL), (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (30 mg) and THF (2 mL). Triethylamine (11 μL) was added and the reaction mixture was shaken overnight at rt. After this time, the resulting solution concentrated and purified by preparative silica gel chromatography (100% EtOAc to 20% MeOH/CH2Cl2) to provide Example 511. MS found: (M+H)+=450.2.