Boc-DL-valine → HCID 86656007, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][CH:17]([CH3:48])[C:18]([NH:20][CH:21]([CH2:38][C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[CH:41][C:40]=1[F:47])[CH2:22][C:23](=[O:37])[N:24]1[CH2:29][CH2:28][N:27]2[C:30]([C:33]([F:36])([F:35])[F:34])=[N:31][N:32]=[C:26]2[CH2:25]1)=[O:19]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:12])[NH:16][CH:17]([C:18](=[O:19])[NH:20][CH:21]([CH2:38][C:39]1[CH:44]=[C:43]([F:45])[C:42]([F:46])=[CH:41][C:40]=1[F:47])[CH2:22][C:23](=[O:37])[N:24]1[CH2:29][CH2:28][N:27]2[C:30]([C:33]([F:35])([F:34])[F:36])=[N:31][N:32]=[C:26]2[CH2:25]1)[CH3:48])[CH:13]([CH3:15])[CH3:14])([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-tert-Butoxycarbonylamino-3-methyl-butyric acid (0.390 gm, 0.00179 moles) in CH2Cl2 (40 ml) was added at 0° C. The reaction mixture was then stirred for 15 minutes. To this stirred solution was added 2-Amino-N-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-propyl]-propionamide (0.860 gm, 0.00179 moles) at 0° C. The reaction mixture was then stirred for overnight. Dicyclohexyl urea was removed by filtration and filtrate was concentrated in vacuum. The residue was purified by silica gel chromatography using CH2Cl2/MeOH (9.7/0.3) as an eluent to yield (2-Methyl-1-{1-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)-propylcarbamoyl]-ethylcarbamoyl}-propyl)-carbamic acid tert-butyl ester (Compound of formula 7) (Yield=0.7 gm, 58%)