Reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:19])[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:41][C:42]1[CH:58]=[CH:57][C:45]([CH2:46][N:47]2[CH2:51][CH2:50][C@@H:49]([NH:52][C:53](=[O:56])[CH2:54][NH2:55])[CH2:48]2)=[CH:44][CH:43]=1>C(Cl)(Cl)Cl>[Cl:41][C:42]1[CH:58]=[CH:57][C:45]([CH2:46][N:47]2[CH2:51][CH2:50][C@@H:49]([NH:52][C:53](=[O:56])[CH2:54][NH:55][C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]([N:9]([CH3:8])[CH3:19])=[CH:18][CH:17]=3)[CH2:48]2)=[CH:44][CH:43]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Triethylamine (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) were added to a chloroform (2 mL) solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (13.8 mg, 0.052 mmol). The resulting reaction mixture was stirred at room temperature for 15 hours. The solution was washed with a 2 M aqueous solution of NaOH (2 mL×2) and brine (2 mL), filtered through a PTFE membrane by using dichloromethane (3 mL), dried and concentrated to thereby afford (R)-1-(4-chlorobenzyl)-3-[[N-(4-dimethylaminobenzoyl)glycyl]amino]pyrrolidine (Compd. No. 952) (24.9 mg). The purity was determined by RPLC/MS (91%). ESI/MS m/e 415.0 (M++H, C22H27ClN4O2).
Workup
- customThe resulting reaction mixture
- washThe solution was washed with a 2 M aqueous solution of NaOH (2 mL×2) and brine (2 mL)
- filtrationfiltered through a PTFE membrane
- customdried
- concentrationconcentrated to thereby afford (R)-1-(4-chlorobenzyl)-3-[[N-(4-dimethylaminobenzoyl)glycyl]amino]pyrrolidine (Compd. No
Sources & evidence
- ORD record
- ord-b671aa3acbe34aa1971abf0b5014f2ec
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390830B1
Linked notes
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