Heteroarene-2-sulfonyl chlorides (BtsCl; ThsCl): Reagents for nitrogen protection of >99% racemization-free phenylglycine activation with SOCl2

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9796-9797

  Vedejs, Edwin ^a   Lin, Shouzhong ^a   Klapars, Artis ^a   Wang, Jiabing ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE DERIVATIVE; PHENYLGLYCINE;

ARTICLE; ISOMERISM; PROTEIN STRUCTURE;

EID: 0029909240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961485n     Document Type: Article

References (43)

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32. (R)-Phenylglycine (0.483 g, 3.20 mmol) was dissolved in 0.25 M aqueous NaOH (11 mL, 2.8 mmol) at 10 °C. Solid 1 (1.10 g, 4.72 mmol) was added, and the suspension was stirred for 10 h at 10 °C while the pH was monitored and 1.3 M NaOH was added to maintain pH 10-10.5 (1.09 g, 97%), mp 162-165.5 °C (dec) after acidification and recrystallization.
33. Product is water soluble; good yield requires evaporation of water.
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38. 2. A chloride/fluoride reactivity advantage of 99:1 was established by NMR.
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40. Glutathione and cysteine are known to cleave unsubstituted heteroarenesulfonamides derived from 1 and 2 by a nucleophilic mechanism: Colucci, D. F.; Buyske, D. A. Biochem. Pharmacol. 1965, 14, 457. Conroy, C. W.; Schwam, H.; Maren, T. H. Drug Metab. Disp. 1984, 12, 614. We thank a referee for these citations and for other valuable comments.
41. Glutathione and cysteine are known to cleave unsubstituted heteroarenesulfonamides derived from 1 and 2 by a nucleophilic mechanism: Colucci, D. F.; Buyske, D. A. Biochem. Pharmacol. 1965, 14, 457. Conroy, C. W.; Schwam, H.; Maren, T. H. Drug Metab. Disp. 1984, 12, 614. We thank a referee for these citations and for other valuable comments.
42. 2O-THF).
43. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley & Sons, Inc.: New York, 1991.