Trifluoroacetic acid → 2-(S)-[(5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)-propionic acid

HRID 1693486Notes

Reaction equation

HRID 1693486 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:36])[C@@H:14]([NH:23][C:24]([C:26]1[NH:35][C:29]2=[N:30][CH:31]=[C:32]([Cl:34])[CH:33]=[C:28]2[CH:27]=1)=[O:25])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)(C)(C)C>C(Cl)Cl>[Cl:34][C:32]1[CH:33]=[C:28]2[CH:27]=[C:26]([C:24]([NH:23][C@@H:14]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:13]([OH:36])=[O:12])=[O:25])[NH:35][C:29]2=[N:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 597535552-(S)-[(5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)-propionic acid tert-butyl ester

Product 1

HCID 597536772-(S)-[(5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.9 mL, 24.3 mmol) was added to a suspension of 2-(S)-[(5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)-propionic acid tert-butyl ester (EXAMPLE 281, 507 mg, 1.21 mmol) in DCM (25 mL) and the reaction mixture was stirred at rt for 16 h. Further trifluoroacetic acid (2 mL) was added and the reaction was stirred at rt for 48 h. The solvent was removed in vacuo and the solid partitioned between 1N hydrochloric acid (50 mL) and ethyl acetate (3×30 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound. δH (CD3OD)-3.11 (1H, dd), 3.33 (1H, dd), 4.88 (1H, m), 6.97 (2H, m), 7.06 (1H, s), 7.28 (2H, m), 8.08 (1H, d), 8.29 (1H, d); m/z (ES+)=362 [M+H]+; RT=3.67 min.

Workup

  1. stirringthe reaction was stirred at rt for 48 h
  2. customThe solvent was removed in vacuo
  3. customthe solid partitioned between 1N hydrochloric acid (50 mL) and ethyl acetate (3×30 mL)
  4. washThe combined organic fractions were washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb9008426d41406f9feabcbae70e5dd5
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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