The Reversible Esterification of Carboxylic Acids with Isobutene and Trimethylethylene. Quantitative Studies and Synthetic Applications

Altschul, Rolf

doi:10.1021/ja01216a054

Cited by 22 publications

(8 citation statements)

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“… bp 35 °C/0.1 mmHg). N -( N -Cbz- l -glutamyl-γ)- l -glutamic acid, as well as compounds 11a , ,, 22 , 24a , , 24b , , 40 , , and 46a , were prepared according to the literature procedure. Experimental details on the synthesis of 46b from 40 , via oxidative elimination of a selenide, are given in the Supporting Information, since such details and spectral data are not available in the literature. , …”

Section: Methodsmentioning

confidence: 99%

“…9H), 1.41-1.46 (m, 9H) 13. C NMR (CDCl 3 ): δ 173 73,. 172.24, 172.22, 172.19, 172.17, 171.17, 171.13, 166.91, 166.83, 155.44, 146.57, 136.66, 131.22, 128.91, 128.48, 128.32, 128.29, 125.40, 82.98, 82.96, 82.94, 81.80, 81.77, 81.75, 80.95, 67.99, 53.88, 53.84, 53.78, 53.74, 53.68, 53.59, 51.74, 51.69, 51.55, 51.50, 39.89, 39.82, 39.68, 39.65, 37.79, 33.00, 32.96, 32.91, 30.69, 30.30, 30.23, 29.96, 29.80, 29.70, 29.58, 29.51, 28.46, 28.41, 28.37, 25.21, 25.01, 24.94, 24.78, 24.49, 24.11, 24.05.…”

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confidence: 99%

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Prodrug Forms of N-[(4-Deoxy-4-amino-10-methyl)pteroyl]glutamate-γ-[ψP(O)(OH)]-glutarate, a Potent Inhibitor of Folylpoly-γ-glutamate Synthetase: Synthesis and Hydrolytic Stability

Feng

Coward

2005

J. Med. Chem.

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Ester prodrugs of the phosphinate pseudopeptide N- [(4-deoxy-4-amino-10-methyl)pteroyl] glutamate-γ-[ψP-(O)(OH)]-glutarate (1a) were synthesized. H-phosphinic acids derived from NCbz vinyl glycine esters were converted to the desired pseudopeptides by Michael addition to α-methyleneglutarate esters. Pivaloyloxymethyl (POM) ester moieties were incorporated in both the N-terminal and C-terminal fragments prior to formation of either C-P bond. N-Alkylation of the corresponding amides derived from p-(N-methyl)-aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding γ-glutamyl conjugate were also synthesized using the same strategy. All prodrugs were evaluated in Chinese hamster ovary cells. Although the pseudopeptide prodrugs were ineffective, prodrugs of methotrexate and the corresponding γ-glutamyl conjugate were equipotent with the parent compounds. Stability of the prodrugs was investigated in both phosphate buffer and cell line medium to provide a rationale for the observed biological data.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Prodrug Forms of N-[(4-Deoxy-4-amino-10-methyl)pteroyl]glutamate-γ-[ψP(O)(OH)]-glutarate, a Potent Inhibitor of Folylpoly-γ-glutamate Synthetase: Synthesis and Hydrolytic Stability

Feng

Coward

2005

J. Med. Chem.

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“…The mechanism of the addition of benzoic acid to isobutene (2-methylpropene) and to trimethylethylene in the presence of sulfuric acid has been studied. It takes place according to Markownikow's rule (4). Boron fluoride (16,24,107) and hydrofluoric acid ( 16) are recommended as catalysts.…”

Section: Addition Of Acidsmentioning

confidence: 99%

Esterification

Reid¹

1948

Ind. Eng. Chem.

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“…Olefins can be esterifled with carboxylic acids in the presence of an acidic catalyst (Altschul, 1946; Cohen and Mier, 1965;Knight et al, 1953;Raether and Gamrath, 1965). Only secondary esters are formed from this reaction.…”

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confidence: 99%