Expedient enantiospecific synthesis of RP 73613: A new selective non-peptide NK1 antagonist

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7743-7744

  Daubié, Christophe ^a   Mutti, Stéphane ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

RP 73613; TACHYKININ RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030597095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01760-1     Document Type: Article

References (11)

1. (1) (a) Mutti, S.; Daubié, C.; Decalogne, F.; Fournier, R.; Rossi, P. Tetrahedron Lett. 1996, 37, 3125-3128.
2. (b) Tabart, M.; Peyronel, J.F. Bioorga. Med. Chem. Lett. 1994, 4, 673-676.
3. (2) (a) Achard, D.; Grisoni, S.; Hanessian, S.; Moutonnier, C.; Peyronel, J.F.; Tabart, M.; Truchon, A. Rhône-Poulenc Rorer Patent EP 514273 and EP 514274.
4. (b) Peyronel, J.F.; Tabart, M.; Achard, D.; Malleron, J.L.; Grisoni, S.; Carruette, A.; Montier, F.; Moussaoui, S.; Fardin, V.; Garret, C. J.F. Eur. J. Med. Chem. 1995, 30, 575-585.
5. (3) Bacqué, E.; Paris, J.M. Synth. Comm. 1992, 22, 2259-2272.
6. (4) The chemical yield and diastereomeric ratio were determined by HPLC analysis.
7. (5) Terao, Y. ; Kotaki, H. ; Imai, N. ; Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896-898.
8. (6) Peyronel, J.F.; Truchon, A.; Moutonnier, C.; Garret, C. Bioorga. Med. Chem. Lett. 1992, 2, 37-40.
9. (7) The enantiomeric purity was determined by HPLC using a chiral phase. This work has been performed by G. Ducrotoy.
10. (8) Concurrently, combination of n-perfluorobutanesulfonyl fluoride and DBU has been shown to be efficient to convert alcohols into their corresponding fluorides : Bennua-Skalmowski, B.; Vorbrüggen, H. Tetrahedron Lett. 1995, 36, 2611-2614.
11. 4 : C67.47, H6.51, N4.14, F2.81 found : C67.11, H6.67, N4.17, F2.78.