Methylamine → N-[N-(3,5-dichlorophenyl)-D,L-alanyl]-(S)-2-aminohexan (N-methyl)-amide

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]([C:12]([OH:14])=O)[CH3:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:15][NH:16][C:17](=O)[C@H:18]([CH2:20][CH2:21][CH2:22][CH3:23])[NH2:19].C(N[C@H](C(O)=O)CCCC)(OC(C)(C)C)=O.CN>>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH:10]([C:12]([NH:19][C@H:18]([CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])=[O:14])[CH3:11])[CH:3]=[C:2]([Cl:1])[CH:7]=1.[CH3:15][NH-:16]

Participants

Reactant 4

HCID 6329Methylamine

HCID 2733747N-tert-Butoxycarbonyl-L-norleucine

HCID 15484844N-(3,5-dichlorophenyl)-D,L-alanine

HCID 18341173l-Norleucine n-methyl amide

Product 1

HCID 131721932N-[N-(3,5-dichlorophenyl)-D,L-alanyl]-(S)-2-aminohexan (N-methyl)-amide

Procedure

Following General Procedure D and using N-(3,5-dichlorophenyl)-D,L-alanine and L-norleucine N-methyl amide (prepared by coupling BOC-L-norleucine (Bachem) with methylamine (Aldrich) using General Procedure E, followed by removal of the BOC group using General Procedure F), the title compound was prepared. The reaction was monitored by tlc (Rf=0.25 in 3% methanol/dichloromethane) and purification of this compound was by thin layer chromatography with 3% methanol/dichloromethane.