Trifluoroacetic acid → HCID 135899506, compound

HRID 2272812Notes

Reaction equation

HRID 2272812 reaction equation
FC(F)(F)S(O)(=O)=O.COC1C=CC(C[N:16]([C:35]2[CH:36]=[N:37][C:38]3[C:43]([CH:44]=2)=[CH:42][CH:41]=[C:40]([O:45]CC2C=CC=CC=2)[CH:39]=3)[C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)[CH:19]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:45][C:40]1[CH:39]=[C:38]2[C:43]([CH:44]=[C:35]([NH:16][C:17](=[O:34])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=4)[CH:19]=3)[CH:36]=[N:37]2)=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 25140250HCID 25140250, compound

Product 1

HCID 135899506HCID 135899506, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic acid (120 μl, 204 mg, 1.36 mmol) was added to 32 (184 mg, 0.30 mmol) in 1:1 CH2Cl2:TFA (1.36 mL) and the solution was stirred at room temperature for two hours. The resulting solution was diluted with CH2Cl2 (100 mL), washed with saturated aqueous NaHCO3 (3×50 mL), saturated aqueous NaCl solution (2×50 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 100:1 EtOAc:MeOH to 4:1 EtOAc:MeOH) to give 34 as a yellow oil (51 mg, 43%): 1H NMR (CD3OD, 500 MHz) δ 9.01 (bs, 1H), 8.61 (bs, 1H), 8.02 (dd, J=8.5, 1.7 Hz, 1H), 7.97 (d, J=1.9 Hz, 1H), 7.74 (d, J=8.9 Hz, 1H), 7.30 (t, J=8.2 Hz, 1H), 7.27 (d, J=1.9 Hz, 1H), 7.19 (dd, J=8.9, 2.1 Hz, 1H), 7.17 (d, J=8.8 Hz, 1H), 7.11-7.08 (m, 2H), 6.89 (m, 1H), 3.88 (s, 3H), 3.81 (s, 3H); 13C NMR (CD3OD, 125 MHz) δ 168.7, 161.2, 160.9, 160.2, 147.1, 146.2, 140.5, 132.0, 132.0, 131.5, 130.4, 130.2, 130.1, 128.5, 127.6, 124.2, 123.2, 121.5, 116.5, 113.8, 112.4, 109.7, 56.5, 55.9; IR (film) νmax 3281, 3203, 2930, 2835, 1605, 1545, 1499, 1371, 1252, 1036, 764, 735 cm−1; HRMS (ESI+) m/z: [M+H]+ calcd for C24H20N2O4, 401.1501. found, 401.1481.

Workup

  1. washwashed with saturated aqueous NaHCO3 (3×50 mL), saturated aqueous NaCl solution (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via column chromatography (SiO2, 100:1 EtOAc:MeOH to 4:1 EtOAc:MeOH)

Sources & evidence

ORD record
ord-7a071ce990c64fca93ad236e2467bcdb
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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