Trifluoroacetic acid → HCID 70674682, compound

HRID 2365737Notes

Reaction equation

HRID 2365737 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:37])[C@@H:16]([N:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[C:32]([F:35])([F:34])[F:33])[C:24]2=[O:36])[CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:10]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:18]1([CH2:17][C@H:16]([N:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][C:29]=3[C:32]([F:34])([F:35])[F:33])[C:24]2=[O:36])[C:15]([NH:14][C:11]2[CH:12]=[CH:13][N:9]([CH2:8][CH2:7][C:6]([OH:38])=[O:5])[N:10]=2)=[O:37])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70674683HCID 70674683, compound

Product 1

HCID 70674682HCID 70674682, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-{3-[(S)-3-cyclopentyl-2-(1-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionylamino]-pyrazol-1-yl}-propionic acid tert-butyl ester (prepared as in Example 19, 130 mg, 0.24 mmol) in methylene chloride (3 mL) at room temperature was treated with trifluoroacetic acid (1 mL) and stirred for 3 h at room temperature. The reaction mixture was then diluted with chloroform (3 mL) and washed with an aqueous semi-saturated sodium bicarbonate solution. The organic layer was then dried over magnesium sulfate, filtered to remove the drying agent, and the filtrate concentrated in vacuo to afford 3-{3-[(S)-3-cyclopentyl-2-(1-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionylamino]-pyrazol-1-yl}-propionic acid (66 mg, 58%) as a white semi-solid: HR-ES(+) m/e calcd for C23H25N4O4F3 [M+H]+ 479.1901, observed 479.1901; 1H NMR (400 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.01 (dd, J=7.67, 15.13 Hz, 2H), 7.75 (t, J=7.56 Hz, 1H), 7.53 (d, J=2.13 Hz, 1H), 6.33 (d, J=2.13 Hz, 1H), 4.97-5.11 (m, 2H), 4.70 (d, J=18.11 Hz, 1H), 4.06 (t, J=7.46 Hz, 2H), 2.25 (t, J=7.35 Hz, 2H), 1.05-2.09 (m, 11H).

Workup

  1. washwashed with an aqueous semi-saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. filtrationfiltered
  4. customto remove the drying agent
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-a8b93c7df8e144e9ab2f8c94bffbabc4
Source dataset
uspto-grants-2014_04
Patent number
US08697705B2

Reaction notes

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