Boc-DL-valine → HCID 86656007, compound

HRID 1043398Notes

Reaction equation

HRID 1043398 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

HCID 270655Boc-DL-valineHCID 53476045HCID 53476045, compound

Product 1

HCID 86656007HCID 86656007, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%)

Workup

  1. stirringThe reaction mixture was then stirred for overnight
  2. customDicyclohexyl urea was removed by filtration and filtrate
  3. concentrationwas concentrated in vacuum
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f0b2a5977624400592d229f364c60d8a
Source dataset
uspto-grants-2013_10
Patent number
US08563517B2

Reaction notes

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