Synthesis of p-aminophenyl aryl H-phosphinic acids and esters via cross-coupling reactions: Elaboration to phosphinic acid pseudopeptide analogues of pteroyl glutamic acid and related antifolates

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5748-5758

  Yang, Yonghong ^a   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS; FOLIC ACID; PHOSPHINIC ACIDS; PROTECTING GROUPS; PTEROYL GLUTAMIC ACID;

CATALYSTS; ESTERS; NITROGEN; ORGANIC ACIDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

(4 AMINOBENZOYL)GLUTAMIC ACID; (BROMOMETHYL)PYRIDOPYRIMIDINE; 5 DEAZAFOLATE; 6 (BROMOMETHYL)PTERIDINE; ANILINE; ANILINIUM HYPOPHOSPHITE; ANION; ESTER DERIVATIVE; FOLIC ACID; FOLIC ACID ANTAGONIST; FORMYLPYRIDOPYRIMIDINE; HALIDE; N 2 ACETYL 6 FORMYLPTERIN; N 2 PIVALOYL 6 FORMYLPTERIN; NITROGEN; PALLADIUM; PHOSPHINIC ACID DERIVATIVE; PHOSPHITE; PHOSPHORUS; PTERIDINE DERIVATIVE; SILICATE; UNCLASSIFIED DRUG;

2 METHYLENEGLUTARIC ACID ESTER; ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HYDROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ESTERS; FOLIC ACID; FOLIC ACID ANTAGONISTS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; PHOSPHINIC ACIDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 34547100037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0707840     Document Type: Article

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46. This method is also applicable to glutarate dimethyl esters by completely removing the dimethyl ester under basic condition, followed by removing the P-OMe by TFA.