Trifluoroacetic acid → N-[(S)-2-hydroxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzamide

HRID 558433Notes

Reaction equation

HRID 558433 reaction equation
FC(F)(F)C(O)=O.C([O:12][CH2:13][C@H:14]([NH:21][C:22](=[O:44])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=2)[CH:24]=1)[C:15](=[O:20])[NH:16][CH2:17][CH2:18][OH:19])(C)(C)C>>[OH:12][CH2:13][C@H:14]([NH:21][C:22](=[O:44])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][C:36]([O:39][C:40]([F:42])([F:43])[F:41])=[CH:35][CH:34]=2)[CH:24]=1)[C:15](=[O:20])[NH:16][CH2:17][CH2:18][OH:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67001634N-[(S)-2-t-butoxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]-benzamide

Product 1

HCID 59265195N-[(S)-2-hydroxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzamideYield 57%

Procedure

Trifluoroacetic acid (1 mL) was added to 20 mg of N-[(S)-2-t-butoxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]-benzamide and the mixture was stirred for 20 minutes at room temperature. After removal of the solvent, the resulting residue was purified using a micromass spectrometer (ZMD produced by Micromass) equipped with a gradient high-performance liquid chromatograph 996-600E produced by Waters. The resulting solid was dried under reduced pressure to obtain 9 mg (57%) of N—[(S)-2-hydroxy-1-(2-hydroxyethylcarbamoyl)ethyl]-4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzamide.

Workup

  1. customAfter removal of the solvent
  2. customthe resulting residue was purified
  3. customa micromass spectrometer (ZMD produced by Micromass)
  4. customequipped with a gradient high-performance liquid chromatograph 996-600E
  5. customproduced by Waters
  6. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-f16e4fe318f54ccd9ca508b84afc51bf
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

Loading…