Trifluoroacetic acid → Trifluoroacetic acid

HRID 925067Notes

Reaction equation

HRID 925067 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]([CH:31]=[CH:32][CH:33]=2)[C:16]([N:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[O:17])=[N:4][NH:3]1.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>C(Cl)Cl>[N:18]1([C:16]([C:15]2[CH:14]=[C:13]([CH:33]=[CH:32][CH:31]=2)[CH2:12][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=3[C:2](=[O:1])[NH:3][N:4]=2)=[O:17])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69044227HCID 69044227, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 25151297HCID 25151297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 55A (480 mg, 1.76 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (5 mL). The solution was stirred at room temperature for 1 hour, and was concentrated. 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 353 (M+H)+; 1H NMR (500 MHz, CD3OD): δ 1.68-1.74 (m, 4H), 2.43-2.48 (m, 2H), 2.48-2.54 (m, 2H), 3.19-3.29 (m, 3H), 3.67-3.97 (m, 5H), 4.04 (s, 2H), 7.30-7.33 (m, 1H), 7.33-7.36 (m, 1H), 7.36-7.39 (m, 1H), 7.44 (t, J=7.48 Hz, 1H).

Workup

  1. concentrationwas 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-a51ef55646b748dc8137096c97f78682
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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