Reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:13](=[O:16])[CH2:14][NH2:15])[CH2:8]2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:26][N:27]([CH3:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][C:13](=[O:16])[CH2:14][NH:15][C:32](=[O:33])[C:31]3[CH:30]=[CH:29][C:28]([N:27]([CH3:26])[CH3:37])=[CH:36][CH:35]=3)[CH2:8]2)=[CH:4][CH:3]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (13.8 mg, 0.052 mmol) in CHCl3 (2 mL) was treated with Et3N (0.021 mL, 0.15 mmol), 4-(dimethylamino)benzoic acid (10 mg, 0.061 mmol), EDCI (10.2 mg, 0.053 mmol) and HOBt (7.5 mg, 0.055 mmol). The reaction mixture was stirred at room temperature for 16 h. The solution was washed with 2 N aqueous NaOH solution (2 mL×2) and brine (2 mL), and dried by filtration through a PTFE membrane using CH2Cl2 (3 mL). Concentration afforded the desired material (compound No. 952) (24.9 mg, quant): The purity was determined by RPLC/MS (91%); ESI/MS m/e 415.0 (M++H, C22H27ClN4O2).
Workup
- washThe solution was washed with 2 N aqueous NaOH solution (2 mL×2) and brine (2 mL)
- dry with materialdried by filtration through a PTFE membrane
- concentrationConcentration
Sources & evidence
- ORD record
- ord-c1216aed88664c66a1c17263040677a0
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06451842B1
Linked notes
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