Trifluoroacetic acid → Trifluoroacetic acid

HRID 925069Notes

Reaction equation

HRID 925069 reaction equation
[O:1]=[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([NH:19][C:20]([CH:22]3[CH2:25][CH2:24][N:23]3C(OC(C)(C)C)=O)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[N:4][NH:3]1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[O:1]=[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:12][C:13]2[CH:14]=[C:15]([NH:19][C:20]([CH:22]3[CH2:25][CH2:24][NH:23]3)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[N:4][NH:3]1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69045004HCID 69045004, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 69048261HCID 69048261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 112A (64 mg) in dichloromethane (4 mL) was treated with trifluoroacetic acid (2 mL) at room temperature for 1 hour. The reaction mixture was concentrated and the residue was purified by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0.1% trifluoroacetic acid/CH3CN/H2O) to provide the title compound as a trifluoroacetic acid salt. MS (DCI/NH3) m/z 339 (M+H)+; 1H NMR (300 MHz, CD3OD): δ 1.64-1.73 (m, 4H), 2.36-2.44 (m, 2H), 2.46-2.53 (m, 2H), 2.57-2.69 (m, 1H), 2.81-2.93 (m, 1H), 3.94-4.04 (m, 1H), 3.98 (s, 2H), 4.08-4.20 (m, 1H), 5.07 (dd, J=9.49, 7.80 Hz, 1H), 7.03 (d, J=8.14 Hz, 1H), 7.30 (t, J=7.80 Hz, 1H), 7.41 (t, —1.70 Hz, 1H), 7.49 (dd, J=7.97, 1.53 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0.1% trifluoroacetic acid/CH3CN/H2O)

Sources & evidence

ORD record
ord-06f44c5ca93d413284d33acc64cef525
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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