1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-((N-benzoylleucyl)aminomethyl)-1-(4-chlorobenzyl)pyrrolidine

HRID 279277

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.[C:16]([NH:24][C@H:25]([C:30](O)=[O:31])[CH2:26][CH:27]([CH3:29])[CH3:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.C(Cl)Cl.CCN(CC)CC>[C:16]([NH:24][C@H:25]([C:30]([NH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:31])[CH2:26][CH:27]([CH3:28])[CH3:29])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (22.5 mg, 0.10 mmol) and dl-benzoylleucine (0.12 mmol) in CHCl3; (1 mL) was treated with EDCI (23 mg), HOBt (16.2 mg) and Et3N (15.2 μL), and stirred at 25° C. for 16 h. The reaction mixture was diluted with CH2Cl2 (0.5 mL), washed with 2 N aqueous NaOH solution (2×0.75 mL), dried by filtration through a PTFE membrane and concentrated to afford 2-((N-benzoylleucyl)aminomethyl)-1-(4-chlorobenzyl)pyrrolidine (compound No. 344) (74 mg, quant): The purity was determined by RPLC/MS (85%); ESI/MS m/e 442 (M++H, C25H32ClN3O2).

Workup

washwashed with 2 N aqueous NaOH solution (2×0.75 mL)
dry with materialdried by filtration through a PTFE membrane
concentrationconcentrated

Sources & evidence

ORD record: ord-8b0e48ac4bd74f8581eff5daf22ee696
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362177B1

Linked notes

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