تفاعل #619150

ord-4e71c768d36b4c488ff20fcf0e0e2611

معادلة التفاعل

CC(C)(C)OC(=O)CNCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid tert-butyl ester
Cl
Hydrogen chloride
O=C(O)CNCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
desired compound
المردود 76.0%
O=C(O)CNCc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
{[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-amino}-acetic acid
المردود 76.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزconcentrated
  2. 2
    workup.DISSOLUTIONThe resulting residue was dissolved in a minimum amount of methylene chloride
  3. 3
    أخرىprecipitated with diethyl ether
  4. 4
    أخرىdecanted

الإجراء التجريبي

{[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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE045183E1uspto-grants-2014_10