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(2S,4R)-4-Benzyloxy-1-{(S)-2-[(S)-2-(2-{(S)-2-[3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-acetylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoyl}-pyrrolidine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide[ No CAS ]
General procedure: All protected amino acids were coupled in CH2Cl2 (5 ml) using DCC (2.5 equiv.) and HOBt (2.5 equiv.) until completion (3 h) judged by Kaiser [15] ninhydrin test. After coupling of the appropriate amino acid, Boc deprotection was effected by use of TFA/CH2Cl2 (1:1, 5 ml)) for 5 min first then repeated for 25 min. Following neutralization with 10% TEA/CH2Cl2 three times (5-5 ml of each), the synthetic cycle was repeated to assemble the resin-bond protected peptide. The peptides were cleaved from the resin with simultaneous side chain deprotection by acidolysis with anhydrous hydrogen fluoride (5 ml) containing 2% anisole, 8% dimethyl sulfide and indole at 5 C for 45 min. The crude peptides were dissolved in aqueous acetic acid and lyophilized.
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 1.16667h;Cooling with ice;
Example 2Boc-L-Trp-L-Arg-OMe (KP-3-2)To a stirred solution of Boc-L-Trp-OH (761 mg, 2.5 mmoles), H-L-Arg-OMe dihydrochloride (718 mg, 2.75 mmoles), HOBt (1378 mg, 9 mmoles) and DIPEA (2.05 ml, 12 mmoles) in DMF (5 ml) and dichloromethane (2 ml) cooled on ice was added HBTU (1138 mg, 3 mmoles) in small portions over 10 minutes. The mixture was stirred on ice for 1 hour, 40 ml ethyl acetate was added and the organic phase washed successively with 3×40 ml saturated NaHCO3, 2×30 ml 5% citric acid, 50 ml water and 2×30 ml brine. Evaporation afforded 1.1 g of a white solid
(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate[ No CAS ]
(5S,10S,11S,14S)-11-benzyl-5,14-di-tert-butyl-3,6,13,16-tetraoxo-8-(4-(pyridin-2-yl)benzyl)-2,17-dioxa-4,7,8,12,15-pentaazaoctadecan-10-yl (S)-2-amino-3-(1H-indol-3-yl)propanoate ditrifluoroacetate[ No CAS ]
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