Trifluoroacetic acid → Trifluoroacetic acid

HRID 1844984Notes

Reaction equation

HRID 1844984 reaction equation
COC(=O)C1C=CC(N=[N:11][C:12]2[NH:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:16]=2)=CC=1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>[Pt](=O)=O.CO>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:15]1[N:16]=[C:12]([NH2:11])[NH:13][CH:14]=1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178499563HCID 178499563, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 178499562HCID 178499562, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-methoxycarbonylmethyl-1H-imidazol-2-ylazo)-benzoic acid methyl ester (2 mmol, 604 mg) synthesized above, platinum (IV) oxide (60 mg) and methanol (50 mL) was hydrogenated (60 psi) for two days (another portion of PtO2 was added after one day). Trifluoroacetic acid (TFA) (2 mmol, 0.15 mL) was added to the reaction mixture and it was filtered. The filtrate was concentrated and diluted with water, washed with ether (2×50 mL). Evaporation of the water from the aqueous solution gave the (2-Amino-1H-imidazol-4-yl)-acetic acid methyl ester as a TFA salt. (273.8 mg, 51%). LCMS: 156 (M+1)+.

Workup

  1. customfor two days
  2. additionwas added after one day)
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with water
  6. washwashed with ether (2×50 mL)
  7. customEvaporation of the water from the aqueous solution

Sources & evidence

ORD record
ord-c964f74b49354a449d347cf2f0df61e4
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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