Reaction #619150

Reaction equation

{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid tert-butyl ester

Hydrogen chloride

→

desired compound

Yield 76.0%

{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid

Yield 76.0%

Solvents

methylene chloride

diethyl ether

Conditions

Workup

1. 1
   Concentrationconcentrated
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in a minimum amount of methylene chloride
3. 3
   Otherprecipitated with diethyl ether
4. 4
   Otherdecanted

Procedure

{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid tert-butyl ester (14 mg, 0.03 mmol) was dissolved in methylene chloride. Hydrogen chloride (100 μL, 4N in dioxane) was added and the reaction was stirred at ambient temperature until no ester could be detected. The reaction was diluted with diethyl ether and concentrated. The resulting residue was dissolved in a minimum amount of methylene chloride, precipitated with diethyl ether and decanted. This was repeated to afford 9 mg (69%) of the desired compound. HPLC-MS: m/z 395 (M+1).

Source