Reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]([OH:21])=O)[CH2:13][CH2:12]1)=[O:9].CCN(C(C)C)C(C)C.[NH2:37][CH2:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][OH:43].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:43][CH2:42][C:41]1[CH:40]=[C:39]([CH:46]=[CH:45][CH:44]=1)[CH2:38][NH:37][C:19]([CH2:18][CH2:17][N:14]1[CH2:13][CH2:12][CH:11]([O:10][C:8](=[O:9])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][CH2:15]1)=[O:21]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic acid (0.5 g, 1.36 mmol; prepared as described in Preparation 11) in DCM (200 mL) was added DIPEA (10.7 mL, 6.12 mmol), 3-aminomethylbenzyl alcohol (0.33 g, 1.9 mmol), DMAP (0.14 g, 0.14 mmol) and EDCI (0.364 g, 1.9 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was concentrated, taken up in EtOAc (20 mL) and then washed with K2CO3 (3×10 mL), H2O (1×10 mL), brine (1×10 mL), dried over magnesium sulfate, filtered and concentrated. The mixture was purified on silica gel (7% MeOH/CHCl3) to afford 0.38 g of the title intermediate (57% yield).
Workup
- concentrationThe mixture was concentrated
- washwashed with K2CO3 (3×10 mL), H2O (1×10 mL), brine (1×10 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe mixture was purified on silica gel (7% MeOH/CHCl3)
Sources & evidence
- ORD record
- ord-65bdb9d69c8a49858c6f4b9105224a76
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728144B2
Linked notes
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