Phenylsilane as an active amidation reagent for the preparation of carboxamides and peptides

Tetrahedron Letters

Volumn 47, Issue 43, 2006, Pages 7649-7651

  Ruan, Zheming ^a   Lawrence, R Michael ^a   Cooper, Christopher B ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID; PEPTIDE; SILANE DERIVATIVE;

AMIDATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLID PHASE SYNTHESIS;

EID: 33748742977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.024     Document Type: Article

References (15)

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12. A representative experimental procedure is described for the reaction of (d)-(+)-2-phenylpropanoic acid with benzylamine: To a solution of 2-phenylpropanoic acid (37.6 mg, 0.25 mmol) and benzylamine (27.1 mg, 0.25 mmol) in DMF (2 mL) was added phenylsilane (92.4 uL, 0.75 mmol) slowly. The reaction mixture was stirred for 5 h at room temperature under an argon atmosphere and then the solvent was evaporated. The resulting mixture was purified preparative HPLC to afford (2S)-N-benzyl-2-phenylpropanamide (7) (51.4 mg, 86%) as a white solid (Table 2, entry 7).
13. 9
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