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

HRID 1870329Notes

Reaction equation

HRID 1870329 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

5

Reactant 4

HCID 6329MethylamineHCID 2733747N-tert-Butoxycarbonyl-L-norleucineHCID 15484844N-(3,5-dichlorophenyl)-D,L-alanineHCID 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.

Workup

  1. customprepared
  2. customfollowed by removal of the BOC group
  3. customwas prepared
  4. customThe reaction was monitored by tlc (Rf=0.25 in 3% methanol/dichloromethane) and purification of this compound

Sources & evidence

ORD record
ord-8364464f837f480c8c8e5c1d63b691dd
Source dataset
uspto-grants-2000_08
Patent number
US06096782

Reaction notes

Loading…