A facile and convenient solid-phase procedure for synthesizing nucleoside hydroxamic acids

Tetrahedron Letters

Volumn 39, Issue 44, 1998, Pages 8031-8034

  Khan, Shoeb I ^a   Grinstaff, Mark W ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; NUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SCREENING; DRUG SYNTHESIS;

EID: 0032578745     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01794-8     Document Type: Article

References (31)

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28. (28) 2-chlorotrityl chloride polystyrene resin (0.28g, 1.8 mmol/g loading, Advanced ChemTech) was added to a solution of dry DMF (10 ml) containing N-hydroxyphthalimide (0.4g, 2.5 mmol) and triethylamine (0.25g, 2.5mmol), and stirred for 12 hours. The resin was filtered and subsequently washed with DMF, water, THF, MeOH, and ether. The loaded resin was then suspended in freshly distilled THF (15 ml) and hydrazine hydrated (0.5 ml) was added. After 10 hours the reaction was stopped and the resin was again isolated by filtration and washed with DMF, water, THF, MeOH, and ether. Next, this modified resin was suspended in dry DMF (10 ml) and DIPEA (3.5 mmol) and HOBt (2.5 mmol) were added. The reaction was cooled to -10°C and propiolic acid (2.5 mmol) was added drop-wise followed by DCC (2.5 mmol). The reaction was stirred for 6 hours at -10°C and then the resin was isolated and washed with DMF, DCM, MeOH, and ether to afford 5 (note: the reaction yield is sensitive to temperature).
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30. 13C NMR (DMSO-d6) δ 42 (C≡CCO), 62.2 (C-5′), 70.8 (C-3′), 72 (C-2′), 77.8 (C≡CCO) 79 (C-4′), 86.2 (C-1′), 89.5 (C-5), 146.5 (C-6), 152 (C-2), 154.8 (C-4), 162 (CONHOH).
31. (31) For a review of Combinatorial Chemistry see the Acc. Chem. Res. Special Issue (1996, volume 29, number 3.)