Trifluoroacetic acid → HCID 178434010, compound

HRID 49389Notes

Reaction equation

HRID 49389 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[NH:22][C:21]([CH3:23])=[N:20][N:19]=2)=[CH:13][CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:23][C:21]1[NH:22][C:18]([CH2:17][C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][NH2:7])=[CH:12][CH:13]=2)=[N:19][N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178434012HCID 178434012, compound

Product 1

HCID 178434010HCID 178434010, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-{2-[4-(5-methyl-4H-[1,2,4]triazol-3-ylmethyl)-phenoxy]-ethyl}-carbamate (380 mg, 1.14 mmol) in methylene chloride (10 ml) was added trifluoroacetic acid (1.7 ml). The resulting mixture was stirred for about thirty minutes and was then concentrated in vacuo. The resulting crude oil was then dissolved in ethyl acetate and brought to pH 10 with aqueous sodium hydroxide. The aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 120 mg (45% yield) of the amine product. LRMS ([M+H]+)=233.1.

Workup

  1. concentrationwas then concentrated in vacuo
  2. dissolutionThe resulting crude oil was then dissolved in ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-155ca355d8ed493bbf054b4ab079b971
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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