Trifluoroacetic acid → HCID 21843640, compound

HRID 2267282Notes

Reaction equation

HRID 2267282 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[CH:14](O)[CH2:13][NH:12][C:11]1=[O:16])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][NH:12][C:11]1=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60204244[2-(5-Hydroxy-2-oxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 21843640HCID 21843640, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[2-(5-Hydroxy-2-oxo-imidazolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (7.85 g, 32 mmol) was suspended in DCM (250 mL) and a solution of TFA (100 mL) in DCM (250 mL) was added over 10 min to the stirred suspension, which dissolved. The solution was stirred for 16 h, concentrated, and azeotroped with MeCN. The resulting TFA salt of the product was dissolved in MeOH (10 mL) and purified on 50 g of SCX resin, washing with MeOH and eluting off with 2 M NH3 in MeOH. Concentration gave the product as a pale yellow oil (3.66 g, 90%). MS (M+H)+ 128.

Workup

  1. dissolutiondissolved
  2. concentrationconcentrated
  3. customazeotroped with MeCN
  4. dissolutionThe resulting TFA salt of the product was dissolved in MeOH (10 mL)
  5. custompurified on 50 g of SCX resin
  6. washwashing with MeOH
  7. washeluting off with 2 M NH3 in MeOH
  8. concentrationConcentration

Sources & evidence

ORD record
ord-b10d14a43ddb458a84cdc89b040c3397
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…