An efficient procedure for the guanylation of amines using N,N′-bis(benzyloxycarbonyl)-S-methylisothiourea

Synthetic Communications

Volumn 26, Issue 14, 1996, Pages 2613-2616

  Chandrakumar, Nizal S ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030010565     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004576     Document Type: Article

References (12)

1. "The Organic Chemistry of Drug Synthesis"; Lednicer, D.; Mitscher, L.A., Eds.; Wiley: New York, Vol.I (1977) and Vol II (1980). For specific examples see references 1, 2, 3 quoted in ref.5
2. "The Organic Chemistry of Drug Synthesis"; Lednicer, D.; Mitscher, L.A., Eds.; Wiley: New York, Vol.I (1977) and Vol II (1980). For specific examples see references 1, 2, 3 quoted in ref.5
3. For a list of references see: (a) Poss, M.A; Iwanowicz, E.; Reid, J.A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933; (b) Bernatowicz, M,s.; Wu, Y.; Matsueda, G. R.; J. Org. Chem. 1992, 57, 2497. For the preparation of guanidines from alcohols see: Dodd, S. D.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977.
4. For a list of references see: (a) Poss, M.A; Iwanowicz, E.; Reid, J.A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933; (b) Bernatowicz, M,s.; Wu, Y.; Matsueda, G. R.; J. Org. Chem. 1992, 57, 2497. For the preparation of guanidines from alcohols see: Dodd, S. D.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977.
5. For a list of references see: (a) Poss, M.A; Iwanowicz, E.; Reid, J.A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933; (b) Bernatowicz, M,s.; Wu, Y.; Matsueda, G. R.; J. Org. Chem. 1992, 57, 2497. For the preparation of guanidines from alcohols see: Dodd, S. D.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977.
6. Iwanowicz, E.; Poss, M.A; Lin, J. Synthetic Communications 1993, 23(10), 1443.
7. (a) Tian, Z.; Edwards, P.; Roeske, R. W. Int. J. Peptide Protein Res. 1992, 40, 119.
8. (b) Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700.
9. Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Hansel, S. B.; Vyas, D. M. Bioorg, Med. Chem. Lett. 1985, 1994.
10. 2-General procedure: To a stirred solution of 1 equivalent of an amine and 2 in dimethylformamide at room temperature was added 1 equivalent of mercuric chloride and 2 equivalents of triethylamine. The reaction was monitored by TLC. After completion of the reaction (about 30 min.), the mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water (2 X), dried and concentrated. The residue was purified by flash chromatography (Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923).
11. 5 66.50 5.35 9.69 66.34 5.31 9.70 a. For 4c: Calculated for Br: 16.57; Found: 16.34. For 4e: Calculated for Cl: 7.36; Found: 7.33.
12. Hofmann, K; Peckham, W. D.; Rheiner, A. J. Am. Chem. Soc. 1956, 78, 238.