Trifluoroacetic acid → HCID 70674682, compound

HRID 1261503Notes

Reaction equation

HRID 1261503 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-6ad1b788a7b247cc959d363dc82d84ac
Source dataset
uspto-grants-2013_06
Patent number
US08470866B2

Reaction notes

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