1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate

Reaction equation

[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[NH:18][NH2:19].CCN=C=NCCCN(C)C>C(#N)C>[C:1]([NH:8][C@H:9]([C:14]([NH:19][NH:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])[CH2:10][CH2:11][S:12][CH3:13])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

Procedure

A solution of Boc-L-methionine (9.972 g) [Boc:tert-butoxycarbonyl] and tert-butyl carbazate (5.29 g) in acetonitrile (100 ml) was combined with WSC (9.202 g) and stirred at room temperature for 5 hours. The reaction mixture was concentrated and the resultant residue was combined with ethyl acetate and water, and the organic phase was washed with water, aqueous sodium bicarbonate and brine, dried and concentrated to obtain tert-butyl 2-(Boc-L-methionyl)-1-hydrazine carboxylate as a colorless oil.