Pictet-Spengler reaction on solid support

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5041-5044

  Yang, Lihu ^a   Guo, Liangqin ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE; BETA LACTAM; HYDANTOIN DERIVATIVE; PIPERAZINEDIONE; PYRROLIDINE DERIVATIVE; TETRAHYDROFURAN; TRYPTOPHAN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; OLIGOMERIZATION;

EID: 0030586143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01012-X     Document Type: Article

References (26)

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21. 2) is precluded, since the cyclization may occur rapidly under the cleavage conditions and give a false positive results. A parallel solution reaction of tryptophan benzyl ester and benzaldehyde under similar conditions gave the intermediate imine as the major product and unreacted starting material after 1 day.
22. 16 Massiot, G. and Mulamba, T. J. Chem. Soc. Chem. Commun. 1983, 1147.
23. 17 Boc-L-Trp-Merrifield resin was purchased from Bachem Bioscience Inc. with loading capacity of 0.61 mmol/g. To increase the utility of this reaction in combinatorial chemistry, other substituted tryptophans were tested with equally good results. Generally, the substituted tryptophans were first converted to the N-Boc derivative followed by attaching to the Merrifield resin under standard conditions.
24. 18 A small amount of resin was cleaved as described later at this step to check purity.
25. 19 The structure was confirmed by oxidation of the tetrahydro-β-carboline with DDQ on solid support followed by cleavage. Details will be reported in due course.
26. 20 Analysis was performed using a Zorbax RX-C8 (250x4.6 mm, 5 μm) column eluting with a linear gradient of 20-80% acetonitrile in water containing 0.1% TFA as buffer over 30 minutes at 1 mL/min, the HPLC is equipped with PDA detector and the results are plotted at 220 nm with band width of 8 nm.