Trifluoroacetic acid → HCID 67479129, compound

HRID 1019654Notes

Reaction equation

HRID 1019654 reaction equation
[CH3:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:15][N:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]4[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=4)[N:17]=3)[CH2:13][CH2:12][N:11]2C(OC(C)(C)C)=O)=[O:9])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([CH:10]2[CH2:15][N:14]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]4[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=4)[N:17]=3)[CH2:13][CH2:12][NH:11]2)=[O:9])=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 67479074HCID 67479074, compound

Product 1

HCID 67479129HCID 67479129, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.4 (43 mg, 0.073 mmol) in DCM was added TFA (10.8 μL, 0.145 mmol). The resulting solution was stirred at room temperature. After 18 hours, additional TFA (0.145 mmol) was introduced. After 30 hours, the reaction was concentrated. The material was brought up in MeOH (2 mL) and filtered through a Si-carbonate cartridge to give 2 in 89% yield. 1H NMR (300 MHz, CDCl3) δ ppm 1.86 (br. s., 1H) 2.31 (s, 3H) 2.79-3.07 (m, 2H) 3.25-3.37 (m, 1H) 3.40-3.54 (m, 2H) 3.75-3.97 (m, 10H) 4.09-4.22 (m, 1H) 4.39 (d, J=5.41 Hz, 2H) 6.10 (d, J=6.14 Hz, 1H) 6.87 (s, 2H) 7.11 (s, 4H) 7.26-7.34 (m, 1H) 8.00 (d, J=5.99 Hz, 1H); M+H 493.25580.

Workup

  1. waitAfter 30 hours
  2. concentrationthe reaction was concentrated
  3. filtrationfiltered through a Si-carbonate cartridge
  4. customto give 2 in 89% yield

Sources & evidence

ORD record
ord-83c1fef5122c4356aa3e92418c67dd04
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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