Glycine tert-butyl ester hydrochloride → Ureido-acetic acid tert-butyl ester

HRID 472759Notes

Reaction equation

HRID 472759 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].[O-:11][C:12]#[N:13].[K+]>O>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:12]([NH2:13])=[O:11])([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 2725036Glycine tert-butyl ester hydrochlorideHCID 11378442Potassium cyanate

Product 1

HCID 86641479Ureido-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of glycine tert-butyl ester hydrochloride (15.13 g, 89.5 mmol) in water (12 ml), a warm solution of potassium cyanate (8.89 g, 107.4 mmol) in water (12 ml) is added in one portion. The clear solution is heated to 65° C. to 70° C. for 15 minutes before removing from heat and cooling to 0° C. in an ice bath. MeOH (approximately 5 ml) is added to dissolve the oil formed and the mixture allowed to sit at 0° C. The crystals formed are filtered, washed with ice water (3×2 ml) and dried to give the title compound; [M+H]+ 174

Workup

  1. temperatureThe clear solution is heated to 65° C. to 70° C. for 15 minutes
  2. custombefore removing
  3. temperaturefrom heat
  4. additionMeOH (approximately 5 ml) is added
  5. dissolutionto dissolve the oil
  6. customformed
  7. customto sit at 0° C
  8. customThe crystals formed
  9. filtrationare filtered
  10. washwashed with ice water (3×2 ml)
  11. customdried

Sources & evidence

ORD record
ord-327e0f14db974163979d9ddcc2394d20
Source dataset
uspto-grants-2014_01
Patent number
US08633211B2

Reaction notes

Loading…