Triethylamine reaction

A series of 5-acyl-2-amino-l,3-selenazoles 331 are prepared from selenazadienes 327 upon treatment with a-haloketones 328 in hot methanol or acetonitrile. In the presence of triethylamine, reaction of selenoazadienes 332 with l,3-dichloro-propan-2-one (5 equiv) affords the bis(selenazoyl) ketones 333 in high yields, whereas the same reaction without base produces the corresponding selenazoles 331 (R3 = CH2CI) preferentially <06S31>. 

Good yields for the 3-aminothietane 1,1-dioxides can be expected by the reaction of phenylmethanesulfonyl chloride with rrans-/S-dimethylamino-styrene in the presence of triethylamine. Reaction proceeds by the pathway given in Scheme 1. 

The first [M Dm3(ttnFe)2](C104)2 complexes of this type were obtained [79] by the interaction of iron(II) acetate and copper, zinc, nickel, cobalt, and manganese acetates with dimethylglyoxime and 1,4,7-trimethyl-1,4,7-triazacyclononane ttn) in methanol in the presence of triethylamine (Reaction 20). In this case, a triazamacrocycle served as the protecting group in the octahedral capping nFe "03 fragment. 

A certain number of recognition phenomena involve sugar sulfates. Synthetic examples are found in Chapter 17. Hydrogensulfates are prepared by treating an alcohol dissolved in DMF with sulfur trioxide in the presence of triethylamine (reaction 5.9). 

The reaction of ketenes with pyridine gives observable intermediates (Scheme 4.35), with a rate constant for 24 at 25 °C of 1.31 X 10 (Table 4.8). Triethylamine reactions with phenylketene and 4-methoxyphenylketene were also reported, with rate constants for zwit-terion formation at 23 °C of 2.3 X 10 s and 2.8 x 10 s, ... 

Scheme 5.34 Decomposition of p-biphenylboronic acid in presence of copper(ll) acetate and triethylamine. Reaction of biphenylboronic acid in the absence of substrates.

DPC 961 (134, Scheme 2.21) has shown activity against wild-type HIV-1 and various non-nucleoside reverse transcriptase inhibitor-resistant HIV strains, and with greater potency than the structurally related efavirenz (Sustiva Bristol-Myers Squibb), an approved drug for HIV treat-ment. ° To facilitate the development of DPC 961, researchers at DuPont Pharmaceuticals Company (Wilmington, DE) developed an asymmetric conjugate addition strategy to introduce the trifluoromethyl amine stereocenter. As depicted in Scheme 2.21, treatment of the known aniline 128 ° with two equivalents of (R)-(-l-)-a-methylbenzyl isocyanate 129 afforded the hemiami-nal 130, which was subsequently converted into the 2(3//)-quinazolinone 131 by reaction with thionyl chloride and triethylamine. Reaction of the quinazolinone 131 with excess cyclopropylacetylene magnesium chloride 132 provided the dihydroquinazolinone 133 in 86% yield and 92% diastereomeric excess. Conversion of the dihydroquinazolinone 133 into DPC 961 134 involved treatment with tri-fluoroacetic acid or warm formic acid. Overall, this process provided 16 kg of DPC 961 134 in >55% overall yield from aniline 128. 

P-Eliminations. 3-Elimination of the hydroxy group of TV-protected p-hydroxy-a-amino acids has been effected using DSC and Triethylamine. Reaction of Z-threonine with equimolar DSC/EtyN in acetonitrile gave exclusively the (Z)-isomer of Z-DBut-OMe (eq 4). Similarly, use of a 1 2 molar ratio of DSC gave the (Z)-isomer of Boc-DBut-OSuc, which on treatment with the methyl ester of alanine gave Z-DBut-Ala-OMe (eq 5). 

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