5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester → 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

HRID 631935Notes

Reaction equation

HRID 631935 reaction equation
C([O:8][C:9]([C:11]1[N:12]([CH3:34])[N:13]=[N:14][C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=[O:10])C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:32]([O:31][C:29]([CH2:28][CH:25]1[CH2:24][CH2:23][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]3[N:14]=[N:13][N:12]([CH3:34])[C:11]=3[C:9]([OH:10])=[O:8])=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)=[O:30])[CH3:33]

Participants

5

Reactant 2

HCID 715003785-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 715005385-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester (51 mg, 0.11 mmol) and 10% Pd/C (58.8 mg, 0.552 mmol) was added ethyl acetate (5 mL) at room temperature under nitrogen atmosphere. Then, the nitrogen was replaced with a hydrogen gas balloon and the black reaction mixture was stirred for 15 h under hydrogen atmosphere at which time TLC analysis indicated the absence of the starting material. Then, the reaction mixture was filtered and the charcoal was washed with a hot ethyl acetate (50 mL), THF (25 mL), CH3CN (75 mL), and ethanol (25 mL). The filtrate was concentrated under vacuum and the residue was dried under high vacuum to obtain 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (40 mg, 97.5% yield) as a white solid. LC/MS calcd. for C20H25N3O4 (m/e) 371, obsd. 372.3 [M+H, ES+].

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. washthe charcoal was washed with a hot ethyl acetate (50 mL), THF (25 mL), CH3CN (75 mL), and ethanol (25 mL)
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-8604d89a1d04412a927d933c5f0cecf8
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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