Enantioselective synthesis of a pyrrolo-benzothiadiazine derivative S 18986, a new AMPA receptor positive modulator

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 24, 1996, Pages 3003-3008

  Desos, P ^a   Serkiz, B ^a   Morain, P ^a   Lepagnol, J ^a   Cordi, A ^a  

^a INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 3,4 CYCLOPENTANO 1,2,4 BENZOTHIADIAZINE 1,1 DIOXIDE; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; BENZOTHIADIAZINE DERIVATIVE; CYCLOTHIAZIDE; KAINIC ACID; N METHYL DEXTRO ASPARTIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHYSIOLOGY; ENANTIOMER; FROG; GENE EXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OOCYTE; RAT; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030591837     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00547-1     Document Type: Article

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29. D = +260° (0.5 mg/ml 95% ethanol). 1H NMR (DMSO-d6) δ 7.55 (dd, 1H), 7.5 (broad s, 1H), 7.4 (td, 1H), 6.75 (td, 1H), 6.7 (dd, 1H), 5.0 (m, 1H), 3.5 (m, 1H), 3.2 (m, 1H), 2.3 (m, 1H), 1.7-2.2 (m, 3H). Extraction of chiral ligand 15: Neutralization of the acid extract of the reaction gave precipitation of a first part of chiral amino alcohol 15 (15.77 g, 65%) and extraction of the filtrate with ethyl acetate gave a second part (7.33 g, 30%).
30. 25 Enantiomeric purity of amino alcohol 15 was monitored as described in ref 13