Process for preparing substituted N-ethyglycine derivatives

Details Process for preparing substituted N-ethyglycine derivatives Process for preparing substituted N-ethyglycine derivatives

1996-09-03

1998-10-06

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Pteroyl per se or having -c-, wherein x is chalcogen, bonded...

544244, 544265, 544276, 544277, 544280, 544311, 544312, 544317, C07D47300, C07D48700, C07D23902

Patent

active

058178112

ABSTRACT:
Processes are described for preparing substituted N-ethylglycine derivatives of the formula ##STR1## in which PG is an amino protecting group which is labile towards weak acids and is of the urethane type or the trityl type, X is NH or O, and B' represents bases which are customary in nucleotide chemistry and whose exocyclic amino and/or hydroxyl groups are protected by suitable known protecting groups, and the salts thereof.

REFERENCES:
Meltzer et al., Peptide Nucleic Acids: Synthesis of Thymine, Adenine Guanine, and Cytosine Nucloebases, The Journal of Organic Chemistry, vol. 60, No. 13, pp. 4305-4308, Jun. 1995.
Finn et al., Synthesis and Properties of DNA-PNA Chimeric Oligomers, Nucleic Acids Research, vol. 24, No. 17, pp. 3357-3363, Sep. 1996.
Breipohl et al., Synthesis of Polyamide Nucleic Acids (PNAs) Using a Novel Fmoc/Mmt Protecting-Group Combination, Bioorganic & Medicinal Chemistry Letters, vol. 6, No. 6, pp. 665-670, Mar. 1996.
Will et al., The Sythesis of Polyamide Nucleic Acids Using a Novel Monomethoxytrityl Protecting-Group Strategy, Tetrahedron, vol. 51, No. 44, pp. 12069-12082, Oct. 1995.
Dueholm et al., Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their Oligomerization, The Journal of Organic Chemistry, vol. 59, No. 19, pp. 5767-5773, Sep. 1994.
Egholm et al., Peptide Nucleic Acids Containing Adenine or Guanine Recognize Thymine and Cytosine in Complementary DNA Sequences, Journal of the Chemical Society Chemical Communications, No. 9, pp. 800-801, May 1993.
J. Jones, The Chemical Synthesis of Peptides, Clarendon Press, Oxford, England, pp. 17-18; 22-23; 26-27; and 33-35, (1991).
S.A. Thompson et al., "Fmoc Mediated Synthesis of Peptide Nucleic Acids," Tetrahedron, vol. 51, No. 22, pp. 6179-6194 (1995).
J. Coste, et al., "PyBOP.RTM.: A New Peptide Coupling Reagent Devoid of Toxic By Product", Tetrahedron Letters, vol. 31, No. 2, pp. 205-208, (1990).
J. Coste et al., "BROP: A New Reagent for Coupling N-Methylated Amino Acids", Tetrahedron Letters, vol. 31, No. 5, pp. 669-672, (1990).
J. Coste, et al., "Oxbenzotriazole Free Peptide Coupling Reagents for N-Mehtylated Amino Acids", Tetrahedron Letters, vol. 32, No. 17, pp. 1967-1970, (1991).
V. Dourtogolou et al., "O-Benzotriazolyl-N, N, N', N'-tetramethyluronium Hexafluorophosphate as Coupling Reagent for the Synthesis of Peptides of Biological Interest", Synthesis, pp. 572-574, (1984).
R. Knorr et al, "New Coupling Reagents in Peptide Chemistry", Tetrahedron Letters, Vlol. 30, No. 15, pp. 1927-1930, (1989).
L.A. Carpino, "1-Hydroxy-7-azabenzotriacole. An Effcient Peptide Coupling Additive", J. Am. Chem. Soc., 115, pp. 4397-4398, (1993).
A. Ehrlich et al., "Synthesis of Cyclic Peptides via Efficient New Coupling Reagents", Tetrahedron Letters, vol. 34, No. 30, pp. 4781-4784, (1993).
Kenich Akaji et al., "Anchoring of Fmoc Amino Acid to 4-Alkoxybenzyl alchol Resing using a New Esterification Reagent", Tetrahedron Letters, vol. 33, No. 22, pp. 3177-3180, (1992).
Louis A. Carpino et al., "((9-Fluroenylmethyl)oxy) carbonyl Amino Acid Chlorides in Solid-Phase Peptide Synthesis", J. Org. Chem, 45, pp. 26-35-2642, (1991).
Jean-Noel Bertho et al., "Preparation and use of N-protected amino acid flurides in peptide synthesis", E. Giralt and D. Andreu (Eds.), Peptides 1990, Escom Science Publisher B. V., pp. 53-54 (1991).
Jeremy Green et al., "Studies on the Acylation of Hydroxy-Functionalized Resins Using Fmoc Amino Acids Activated Using Diisopropylcarbodiimide/HOBt or as Acids Fluorides", Tetrahedron Letters, vol. 49, No. 20, pp. 4141-4146, (1993).
Birgit Blankemeyer-menge et al., "An Efficient Method for Anchoring FMOC-Amino Acids to Hydroxyl-Functionalised Solid Supports", Tetrahedron Letters, vol. 31, No. 12, pp. 1701-1704, (1990).
Derek Hudson, "Methodological Implications of Simultaneous Solid-Phase Peptide Synthesis: A Comparison of Active Esters", Peptides Research, pp. 51-55, (1990).
John E. Bishop et al., "The Reaction of Thioimides with Phosphorus Ylides", J. Org. Chem., 56, pp. 5079-5091, (1991).
A. Paul Krapcho et al., "Mono-Protected Diamines, N-tert-BUTOXYCARBONYL-.sub.a,w- Alkanediamines from .sub.a,w- Alkanediamines", Synthetic Communications, 20(16), pp. 2259-2564, (1990).
Antonio Evidente et al., "Syntheses of cis-Zeatin and Its 9-(Dexy-.beta.-D-ribofuranosyl) Derivative: A Novel Synthetic Route to the Side Chain at C(6), and Cytokinin Acitivity", Chem. Pharm. Bull 40(7), pp. 1937-1939, (1992).

Affiliated with

Also associated with

Rating

Process for preparing substituted N-ethyglycine derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing substituted N-ethyglycine derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing substituted N-ethyglycine derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-79441