Tert-butyl (2-(5-(4-ethoxybenzyl)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate → 3-(2-Aminoethyl)-5-(4-ethoxybenzyl)thiazolidine-2,4-dione

HRID 517573Notes

Reaction equation

HRID 517573 reaction equation
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][CH:9]2[S:13][C:12](=[O:14])[N:11]([CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)[C:10]2=[O:25])=[CH:6][CH:5]=1)[CH3:2]>C(O)(C(F)(F)F)=O.ClCCl>[NH2:17][CH2:16][CH2:15][N:11]1[C:10](=[O:25])[CH:9]([CH2:8][C:7]2[CH:26]=[CH:27][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)[S:13][C:12]1=[O:14]

Participants

4

Reactant 1

HCID 71697069Tert-butyl (2-(5-(4-ethoxybenzyl)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

Product 1

HCID 716970713-(2-Aminoethyl)-5-(4-ethoxybenzyl)thiazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 5 (80 mg, 0.20 mmol) was dissolved in 50% TFA in dichloromethane (2 mL) and then stirred at room temperature for 1 h. The solvent was removed by evaporation and the residue was dissolved in dioxane (2 mL), and evaporated again. The solid was collected by filtration, washed with ethyl ether, and dried to afford compound 6 in 58.5% (48 mg) yield as a white solid.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in dioxane (2 mL)
  3. customevaporated again
  4. filtrationThe solid was collected by filtration
  5. washwashed with ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-c133b610edc146c185eb582907eefc47
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

Loading…