Trifluoroacetic acid → HCID 67172980, compound

HRID 1891266Notes

Reaction equation

HRID 1891266 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][CH2:11][C:12]([O:14]C)=O)[CH3:9])=[CH:4][CH:3]=1.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17].FC(F)(F)C(O)=O>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([N:10]2[CH2:11][C:12](=[O:14])[N:18]([CH2:16][CH3:17])[C:19]2=[O:20])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8022Ethyl isocyanateHCID 28431656HCID 28431656, compound

Product 1

HCID 67172980HCID 67172980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

(R)-Methyl 2-(1-(4-bromophenyl)ethylamino)acetate (6G3) (0.845 mmol, 230 mg) was dissolved in DCM (10 ml) and ethyl isocyanate (6C4) (1.690 mmol, 120 mg) added. The mixture was stirred at room temperature for 3 hours, then concentrated and re-dissolved in DCM (5 ml) and trifluoroacetic acid (0.845 mmol, 96 mg) added. Stirring was continued for 1 h and the reaction diluted with DCM (15 ml) and water (20 ml) and the organic phase separated using a hydrophobic fritted tube. Concentration afforded (R)-1-(1-(4-bromophenyl)ethyl)-3-ethylimidazolidine-2,4-dione (6G4) which was used without further purification; 1H NMR (400 MHz, CDCl3) δ 7.50 (d, 2H) 7.18 (d, 2H) 5.43 (q, 1H) 3.76 (d, 1H) 3.56 (q, 2H) 3.46 (d, 1H) 1.57 (d, 3H) 1.22 (t, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in DCM (5 ml)
  3. stirringStirring
  4. waitwas continued for 1 h
  5. customthe organic phase separated
  6. concentrationConcentration

Sources & evidence

ORD record
ord-8b253c8b152c452c86d79b3af09ba522
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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