A convenient and scalable synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride. Key intermediates for peptide nucleic acid synthesis

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1630-1632

  Viirre, Russell D ^a   Hudson, Robert H E ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

REDUCTIVE ALKYLATION;

ALKYLATION; SALTS; SYNTHESIS (CHEMICAL);

NUCLEIC ACIDS;

ETHYL N [(2 TERT BUTYLOXYCARBONYLAMINO)ETHYL]GLYCINATE; ETHYLENEDIAMINE DERIVATIVE; GLYCINE DERIVATIVE; GLYOXYLIC ACID; NUCLEIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHROMATOGRAPHY; NUCLEIC ACID SYNTHESIS; PRECURSOR; PURIFICATION; SYNTHESIS;

ALKYLATION; CATALYSIS; CHROMATOGRAPHY; GLYCINE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PEPTIDE NUCLEIC ACIDS;

EID: 0037458890     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026590w     Document Type: Article

References (12)

1. For more about the application, properties, and standard syntheses of PNA, see the following review and references therein: Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624-630.
2. tBoc- and Fmoc-PNA monomers are available from Applied Biosystems, Foster City, CA 94404.
3. Dueholm, K. L.; Egholm, M.; Behrens, C.; Christensen, L.; Hansen, H. F.; Vulpius, T.; Petersen, K. H.; Berg, R. H.; Nielsen, P. E.; Buchardt, O. J. Org. Chem. 1994, 59, 5767-5773.
4. Kofoed, T.; Hansen, H. F.; Orum, H.; Koch, T. J. Peptide Sci. 2001, 7, 402-412.
5. Meltzer, P. C.; Liang, A. Y.; Matsudaira, P. J. Org. Chem. 1995, 60, 4305-4308.
6. Kelly, R. K.; Schmidt, T. E.; Haggerty, J. G. Synthesis 1972, 544-545.
7. Wennerberg, J.; Polla, M.; Frejd, T. J. Org. Chem. 1997, 62, 8735-8740.
8. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622-2624.
9. Bailey, P. D.; Smith, P. D.; Pederson, F.; Clegg, W.; Rosair, G. M.; Teat, S. J. Tetrahedron Lett. 2002, 43, 1067-1070.
10. Technical grade ethyl glyoxylate, ∼50% in toluene, is commercially available from Fluka cat. #50705 and Lancaster Synthesis cat. #19207, but this material "exists partly in the polymerized form" (2001/2002 Fluka laboratory chemicals and analytical reagents catalog). We have not yet attempted to synthesize 1 using this product.
11. Viirre, R. D.; Hudson, R. H. E. Org. Lett. 2001, 3, 3931-3934.
12. Hudson, R. H. E.; Li, G.; Tse, J. Tetrahedron Lett. 2002, 43, 1381-1386.