An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins in the solid phase is described. This methodology uses MeSiCI3 in the presence of Et3N to cleave Fmoc-protected amines directly to their isocyanates. Internal cyclization of the amide on the isocyanate follows to produce t
Solid phase urea synthesis: An efficient and direct conversion of Fmoc-protected amines to ureas
โ Scribed by Pek Y. Chong; Peter A. Petillo
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 215 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
An efficient "one-pot" conversion of Fmoc-protected amino acids to the ureas in the solid phase is described. This methodology uses MeSiCI3 in the presence of Et3N to cleave Fmoc-protected amines directly to their isocyanates. This transformation has been demonstrated on some Fmocprotected amino acids. Trapping of the resin-bound isocyanate by the addition of amines generates the desired amino acid ureas in high HPLC purities.
๐ SIMILAR VOLUMES
Support-bound, Fmoc-protected amines react with aliphatic alcohols in the presence of ADDP, PBu 3 , and DIPEA to yield O-alkyl carbamates. The reaction presumably proceeds via O-alkylation of an intermediate carbamate anion.