Methyl 2(s)-ethoxy-3-[4-(2-methyl-5-nitro-2h[1,2,4]triazol-3-yl)phenyl]propanoate → methyl 3-[4-(5-amino-2-methyl-2H-[1,2,4]triazol-3-yl)phenyl]-2(S)-ethoxypropanoate

HRID 910308Notes

Reaction equation

HRID 910308 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]([CH3:24])[N:18]=[C:19]([N+:21]([O-])=O)[N:20]=2)=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]>C(O)C.CO.[Pd]>[NH2:21][C:19]1[N:20]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][C@H:4]([O:3][CH2:1][CH3:2])[C:5]([O:7][CH3:8])=[O:6])=[CH:15][CH:14]=2)[N:17]([CH3:24])[N:18]=1

Participants

5

Reactant 1

HCID 67148279Methyl 2(s)-ethoxy-3-[4-(2-methyl-5-nitro-2h[1,2,4]triazol-3-yl)phenyl]propanoate

Product 1

HCID 67147868methyl 3-[4-(5-amino-2-methyl-2H-[1,2,4]triazol-3-yl)phenyl]-2(S)-ethoxypropanoateYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

0.4 g (0.4 mass equivalent) of 10% palladium-on-charcoal is added to a solution of 0.9 g (2.7 mmol) of methyl 2(S)-ethoxy-3-[4-(2-methyl-5-nitro-2H-[1,2,4]triazol-3-yl)phenyl]propanoate in 40 ml of ethanol and 10 ml of methanol, degassed beforehand, and the reaction medium is placed under an atmospheric pressure of hydrogen for 3 hours. After filtration through Celite and washing with ethyl acetate, the filtrate is evaporated under vacuum. 0.82 g (100%) of methyl 3-[4-(5-amino-2-methyl-2H-[1,2,4]triazol-3-yl)phenyl]-2(S)-ethoxypropanoate is obtained.

Workup

  1. customdegassed beforehand
  2. filtrationAfter filtration through Celite
  3. washwashing with ethyl acetate
  4. customthe filtrate is evaporated under vacuum

Sources & evidence

ORD record
ord-d7c32a74cbed476285ad97ca0fa499e1
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

Loading…