Trifluoroacetic acid → 2-(4-Aminophenyl)-3-(acetylthio)propanoic acid ethyl ester

HRID 1677611Notes

Reaction equation

HRID 1677611 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH:17]C(OCC2C=CC=CC=2)=O)=[CH:13][CH:12]=1)[CH2:6][S:7][C:8](=[O:10])[CH3:9])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[CH2:6][S:7][C:8](=[O:10])[CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86608784HCID 86608784, compound

Product 1

HCID 866087852-(4-Aminophenyl)-3-(acetylthio)propanoic acid ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(benzyloxycarbonylamino)phenyl)-3-(acetylthio)-propanoic acid ethyl ester (0.2 g, 0.54 mmol) in 5 mL of methylene chloride was added 5 mL of trifluoroacetic acid. After 0.5 hours, the reaction mixture was concentrated in vacuo. The compound was purified by flash chromatography through silica gel (1/1 hexanes/ethyl acetate) to afford 2-(4-aminophenyl)-3-(acetylthio)propanoic acid ethyl ester (0.12 g, 85%).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe compound was purified by flash chromatography through silica gel (1/1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f43231db2e964a21af3852bb74f95b32
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

Loading…