Ammonia in Ugi reactions - Four-component versus six-component couplings

Synlett

Volumn , Issue 5, 2005, Pages 757-760

  Pick, Rigobert ^a   Bauer, Michael ^a   Kazmaier, Uli ^a   Hebach, Christina ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Ammonia; Peptide; Six component coupling; Ugi reactions

Indexed keywords

AMMONIA; CYCLOPEPTIDE;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; COUPLING FACTOR; PEPTIDE ANALYSIS; PROTEIN MODIFICATION; PROTEIN STRUCTURE; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; UGI REACTION;

EID: 15944427522     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863722     Document Type: Article

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22. 4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography giving rise to 1a and 3a.
23. 2.
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26. 4). Evaporation of the solvent leads to analytically pure 1a (302 mg, 0.99 mmol, 99%) as a snow white powder.
27. 6): δ = 0.72 (d, J = 6.8 Hz, 3 H), 0.73 (d, 7 = 6.8 Hz, 3 H), 1.95 (m, 1 H), 3.64 (dd, J = 17.9,5.5 Hz, 1 H), 3.68 (dd, 7= 17.9, 5.5 Hz, 1 H), 4.29 (dd, J = 8.8, 7.0 Hz, 1 H), 7.13 (dd, J = 7.5, 7.4 Hz, 2 H), 7.20 (tt, J = 7.4, 1.3 Hz, 1 H), 7.27 (d, J = 8.8 Hz, 1 H), 7.55 (sh, 3 H).
28. 2O (50 mL) filtrated and dried, giving rise to analytically pure 1a (5.2 g, 17 mmol) as a snow white powder.