A’-methylpyrrolidone

Alkenes treated with N2O4 and CaO in oxygenated A-methylpyrrolidone are converted into 3-acyl-2-isoxazolines as in Scheme 122 (78USP4069226). 

This amide, readily formed from an amine and the anhydride, is readily cleaved by penicillin acylase (pH 8.1, A -methylpyrrolidone, 65-95% yield). This depro-tection procedure works on peptides as well as on nonpeptide substrates. 

Sodium sulfide in A -methylpyrrolidone, NMP, (140°, 2-4 h) cleaves aryl methyl ethers in 78-85% yield. ... 

This amide, readily formed from an amine and the anhydride or enzymatically using penicillin amidase, is readily cleaved by penicillin acylase (pH 8.1, A -methylpyrrolidone, 65-95% yield). This deprotection procedure works on peptides, phosphorylated peptides, and oligonucleotides, as well as on nonpeptide substrates. The deprotection of racemic phenylacetamides with penicillin acylase can result in enantiomer enrichment of the cleaved amine and the remaining amide. An immobilized form of penicillin G acylase has been developed. ... 

Mercaptobenzothiazole, A-methylpyrrolidone, DIPEA. The reagent has the advantage that it is odorless and does not lead to intemucleotide cleavage, but the cleavage rate is 10 times slower than when thiophenol is used. ... 

Amine bound to a Wang-polystyrene resin 381 was acylated with 4-oxo-4Ff-pyrido[l,2-u]pyrazine-3-carboxylic acid in the presence of bromotrispyrrolidinophosphonium hexafluorophosphate and /-Pr2NEt in A-methylpyrrolidone (98MIP16). l-(4-Cyclohexyl-4-r / r-butylaminocarbo-nyl-l-piperidyl)-2-(4-fluorophenyl)ethylamine was acylated with perhydro-pyrido[l,2-u]pyrazine-3-carboxylic acid (01MIP19). An amino group of a macrocyclic compound attached to a solid support was acylated with... 

The 3-trifluoromethylsulfonyloxy-3A-cephem 84 is converted to the norcephalosporin 85 at 130 °C and 3-nor-2A-cephalosporin 86 at 0 °C by the action of copper hydride, formed from tributyltin hydride and copper chloride in A-methylpyrrolidone <99JCS(P1)3463>. 

Arosolvan A-Methylpyrrolidone 308 Vertical mixer-settler column... 

A(-Methylsuccinimide was converted to A(-methylpyrrolidone in 92% yield on heating for 18 minutes at 100° with 3 equivalents of sodium bis(2-methoxy-ethoxy)aluminum hydride [544], and A(-phenylsuccinimide was transformed into A -phenylpyrrolidone in 67% yield by electroreduction on a lead cathode in dilute sulfuric acid [1120]. 

The Csajagi research group used a commercial X-Cube continuous flow reactor system [32] to perform similar reactions. The reactor is made of stainless steel, capable of reaching pressures of up to 150 bar, and equipped with preloaded catalyst cartridges. Monoamides of aryldicarboxylic acids are obtained in a reaction over a tetrakis(triphenylphosphine)palladium catalyst using A-methylpyrrolidone as base [33]. Terephtalic acid was reported as the byproduct, but not the oc-ketoamide. 

Malek DE, Malley LA, Slone TW, et al Repeated dose toxicity study (28 days) in rats and mice with A/-methylpyrrolidone (NMP). Drug Chem Toxicol 20(l/2) 63-77, 1997... 

Malley LA, Kennedy GL, Elliott GS, et al 90-Day suhchronic toxicity study in rats and mice fed A/-methylpyrrolidone (NMP) including neurotoxicity evaluation in rats. Drug Chem Toxicol 22(3) 455 80, 1999... 

Fig. 18. Effect of pressure on methanol and ethylene glycol formation rates by an iodide-promoted ruthenium catalyst (191). Reaction conditions 75 ml A -methylpyrrolidone solvent, 15 mmol Ru, 45 mmol Nal, H2/CO = 1, 230 C. 1 MPa = 9.87 atm.

Fig. 26. SEM micrographs illustrating the effects of airborne basic chemical contamination, (a) This image was formed when a positive-tone CA resist was processed without any delay after coating, (b) This image was formed when an identical film was stored after coating for 15 minutes in an atmosphere containing 10 parts per billion on A/-methylpyrrolidone, and then processed identically to the first film.

BPA/DC was compounded with high-temperature resistant ladder and semi-ladder polymers. A composition, which contained BPA/DC, a polyimide resin, organic Zn salt and benzyldimethylamine in A -methylpyrrolidone solution was described. The binder was destined for the manufacture of copper clad laminates. Tg of the cross-linked material was 265 °C [50]. Another example is a binder obtained from BPA/DC and polyphenylquinoxaline in chloroform [51]. 

Electrochemical carbocyclization reactions involving the preparation of 3-, 4-, 5-, or 6-membered rings have been described. The reaction involves complexing of olefinic compounds, such as dimethyl maleate 126 and a,co-dibromide, such as 1,3-dibromopropane 127 in an undivided cell fitted with a sacrificial aluminum anode, in A-methylpyrrolidone at constant current (equation 66)99. The reaction is of special interest for the preparation... 

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