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

HRID 2299554Notes

Reaction equation

HRID 2299554 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 reacticon 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 reacticon was monitored by tlc (Rf=0.25 in 3% methanol/dichloromethane) and purification of this compound

Sources & evidence

ORD record
ord-3d16b1a6e9ba48db9831babdea997ac6
Source dataset
uspto-grants-2002_12
Patent number
US06495693B2

Reaction notes

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