Trifluoroacetic acid → 2-Methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl ester

HRID 502386Notes

Reaction equation

HRID 502386 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:31])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:25])[CH3:24])[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:29]([O:28][C:26](=[O:27])[C:23]([CH3:25])([O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15](=[O:31])[NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:17]=1)[CH3:24])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684578994-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 684563992-Methyl-2-[3-(piperidin-4-ylcarbamoyl)-phenoxy]-propionic acid ethyl esterYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.08 g (5.0 mmol) of 4-[3-(1-ethoxycarbonyl-1-methyl-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester was dissolved under argon in 80 mL of MeCl2; to the stirred solution, 3.66 mL (5.46 g=10 eq.) of TFA was added drop by drop and stirring continued at rt for 5 h. Then, the reaction mixture was evaporated i.V., the residue was dissolved in MeCl2 and water, the pH was adjusted to ˜10 with sodium carbonate solution and the mixture was extracted twice with MeCl2; the organic phases were washed with water, dried over MgSO4, filtered and evaporated i.V. The crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH) to yield 1.20 g of the title compound as colorless oil. MS: 335.2 (MH+).

Workup

  1. customThen, the reaction mixture was evaporated i.V
  2. dissolution, the residue was dissolved in MeCl2
  3. extractionthe mixture was extracted twice with MeCl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated i.V
  8. customThe crude product was purified by chromatography (silicagel, eluent:gradient of MeCl2/MeOH)

Sources & evidence

ORD record
ord-06705bbc4a6b442d887aa0b1afd8a02f
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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