Benzylamine → HCID 86650906, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[CH2:33]([NH:40][C:10](=[O:12])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][O:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1Participants
5
Procedure
To a cold solution (5° C.) of 10.00 g of Intermediate 2 in 150 mL of dichloromethane was added 5.89 g (0.036 mol) of 1,1′-carbonyldiimidazole. The mixture was allowed to warm to room temperature and stirred for 1.5 hours. Then, it was cooled to 5° C. and 4.37 g (0.041 mol) of benzylamine was added dropwise and the reaction was stirred at room temperature overnight. The organic phase was washed with 1 M HCl (2×80 mL), sodium bicarbonate solution (2×80 mL), water (80 mL), brine (80 mL) and dried over sodium sulfate. The solvent was evaporated under vacuum yielding 14.36 g as an oil. The oil was not purified and used directly in the following step.
Workup
- temperatureThen, it was cooled to 5° C.
- stirringthe reaction was stirred at room temperature overnight
- washThe organic phase was washed with 1 M HCl (2×80 mL), sodium bicarbonate solution (2×80 mL), water (80 mL), brine (80 mL)
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under vacuum
- customyielding 14.36 g as an oil
- customThe oil was not purified
Sources & evidence
- ORD record
- ord-0441beb377384f4da3129ef9cbdf19cc
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440861B2
Reaction notes
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