Dipeptide analogues containing 4-ethoxy-3-pyrrolin-2-ones

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2103-2106

  Hosseini, Masood ^a,b   Kringelum, Henriette ^b   Murray, Anthony ^a   Tønder, Janne E ^b  

^a NOVO NORDISK A S   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; AMINO ACID; DIPEPTIDE; PYRROLE DERIVATIVE; TETRAMIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS; THERMODYNAMICS;

AMINO ACIDS; DIPEPTIDES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRROLES; PYRROLIDINONES; THERMODYNAMICS;

EID: 33744722470     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060500i     Document Type: Article

References (28)

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25. Preliminary removal conditions were 10% HBr in MeCN.
26. To a solution of tetramic acid (1 g, 1.0 equiv) in THF (30 mL) at 0 °C was added dropwise KHMDS (0.50 M in toluene, 1.05 equiv), and the suspension was stirred for 10 min at 0 °C. To this was added EtOTs (1.1 equiv) and 18-crown-6 (1.1 equiv), and the mixture was slowly heated to room temperature. Upon completion of the reaction (TLC, EtOAc), the mixture was evaporated with 50 mL of silica, and flash chromatography (EtOAc) provided the pure product.
27. n-BuLi (1.58 M in hexanes, 1.0 equiv) was added dropwise to a solution of H-pyAA-OEt (3) (50 mg, 1.0 equiv) in THF (3 mL) at -55 °C, and stirring was continued for 10 min. To this yellow solution was added Fmoc-AA-OPfp (1.1 equiv) dissolved in THF (2 mL) by a syringe pump over 15 min. The mixture was allowed to stir for an additional 5 min. Over this 30 min period, the temperature had been allowed to reach -45 0C. The mixture was quenched with AcOH (0.1 mL) and evaporated with 5 mL of silica. Column chromatography (30→50% EtOAc in heptane) afforded the pure compounds (4) as white solids.
28. See Supporting Information for details and results of the molecular modeling study.