Trifluoroacetic acid → 3-{3-[1-(2-Amino-3-methyl-butyryl)-pyrrolidin-2-ylmethyl]-benzofuran-2-yl}-propionic acid ethyl ester

HRID 1054007Notes

Reaction equation

HRID 1054007 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[O:8][C:9]2[CH:35]=[CH:34][CH:33]=[CH:32][C:10]=2[C:11]=1[CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18](=[O:31])[CH:19]([NH:23]C(OC(C)(C)C)=O)[CH:20]([CH3:22])[CH3:21])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[O:8][C:9]2[CH:35]=[CH:34][CH:33]=[CH:32][C:10]=2[C:11]=1[CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18](=[O:31])[CH:19]([NH2:23])[CH:20]([CH3:22])[CH3:21])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67148370HCID 67148370, compound

Product 1

HCID 671486353-{3-[1-(2-Amino-3-methyl-butyryl)-pyrrolidin-2-ylmethyl]-benzofuran-2-yl}-propionic acid ethyl esterYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 49 (302 mg, 0.6 mmol) in DCM (10 mL) was added TFA (2 mL) at ambient temperature. After 2 h, the solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 235 mg (97%) of 50 as an orange oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ7.86-7.83 (m, 1H), 7.43-7.34 (m, 1H), 7.27-7.19 (m, 3H), 4.49 (m, 1H), 4.14 (q, J=6.9 Hz, 2H), 3.60-3.53 (m, 2H), 3.32 (d, J=12.9 Hz, 1H), 3.12 (app t, J=7.2 Hz, 2H), 2.81-2.74 (m, 2H), 2.42 (app t, J=12.3 Hz, 1H), 2.10-1.91 (m, 2H), 1.74-1.66 (m, 2H), 1.24 (t, J=7.2 Hz, 3H), 1.06-0.99 (m, 6H) ppm. Mass spectrum: m/z 401 [M+H]+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1961fbfcd8f345838608a998040e6f21
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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