Practical enantiospecific synthesis of RPR 111905: A novel Non-peptide substance P antagonist

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8743-8746

  Mutti, Stéphane ^a   Daubié, Christophe ^a   Malpart, Joël ^a   Radisson, Xavier ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

RPR 11195; SUBSTANCE P ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; DRUG SYNTHESIS; ENANTIOMER; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030602173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02017-5     Document Type: Article

References (16)

1. (1) a/ Mutti, S.; Daubié, C.; Decalogne, F.; Fournier, R.; Rossi, P. Tetrahedron Lett. 1996, 37, 3125-3128.
2. b/ Daubié, C.; Mutti, S. Tetrahedron Lett. Submitted for publication.
3. c/ Tabart, M.; Peyronel, J.F. Bioorga. Med Chem. Lett. 1994, 4, 673-676.
4. (2) Achard, D.; Peyronel, J.F.; Tabart, M. Rhône-Poulenc Rorer Patent FR 94 14345.
5. (3) Mayer, S.C.; Pfizenmayer, A.J.; Cordova, R.; Li, W.R.; Joullié, M.M. Tetrahedron : Asymmetry 1994, 5, 519-522.
6. (4) McDonald, E. ; Suksamrarn, A.; Wilye, R.M. J. Chem. Soc.Perkin Trans I 1979, 1893-1900.
7. (5) The chemical yield and E : Z ratio were determined by GC analysis using an external standard.
8. (6) This salt exists as a monohydrate and is a hemi-salt.
9. (7) The enantiomeric purity was determined by HPLC using a chiral phase, after N-Boc-derivatisation. This work has been performed by M. Descarpentry (Rhône-Poulenc Rorer).
10. (8) a/ Org. Syntheses Coll Vol 4, 1956, 192-195.
11. b/ Org. Syntheses Coll. Vol 3, 1955, 207-209.
12. (9) The chemical yield was determined by HPLC analysis using an external standard.
13. (10) Toussaint, O. Thèse de l'Université Paris VI, 26 Juin 1986.
14. (11) o-Anisylmagnesium bromide was purchased from Chemetall GMBH as a 20% w/w solution in THF.
15. (12) Mutti, S.; Daubié, C.; Decalogne, F.; Fournier, R.; Montuori, O.; Rossi, P. Synth. Comm. 1996, 26, 2349-2354.
16. 4 : C72.30, H7.19, N6.25, found : 71.98, H7.21, N6.19.