2- Methyl-2- propanamides

Fig. 7.20 Illustration of the additivity of conformational geometry functions for the 41-rotation in (CH3NH)(0=)C-C(CH3)(H)(NHCOCH3) (ALA). During the torsional motion about the C(a)-C bond of ALA, the interactions within the system are the same as those encountered during the C(=0)-C torsion in N-methyl propanamide (NMPA), plus those encountered during the C(ct)-C torsion in N-acetyl N -methyl glycine amide offset by 120° as shown (GLY), minus those encountered during the C-C torsion in N-methyl acetamide (NMA).

For the i (-rotation in ALA (Fig. 7.20), the corresponding combination involves N-methyl propanamide, NMPA, plus GLY, minus NMA. For more details concerning the addition of CGF see (Schafer et al. in press, G). 

Smiles rearrangement. The Smiles rearrangement is ordinarily limited to substrates in which the aromatic ring is activated by an electron-withdrawing substituent. However, if HMPT is used as solvent, 2-aryloxy-2-methylpcopana-mides (1) arc rearranged by sodium hydride to N-aryl-2-hydroxy-2-methyl-propanamides (2) in 50-85%, yield. The products are hydrolyzed by acid to anilines (3). ... 

Tasimelteon, (li -trans)-iV-[[2-(2,3-dihy-dro-4-benzofuranyl)cycloproplyl]methyl] propanamide, has high affinity for melatonin MTi and MT2 receptors. 

NaH-dispersion added carefully to a soln. of 2-(benzo[b]thien-4-yloxy)-2-methyl-propanamide in dry hexamethylphosphoramide, and heated 1 hr. on a steam bath N-benzo[b]thien-4-yl-2-hydroxy-2-methylpropanamide. Y 72%. - This is a stage of a 4-step sequence for the prepn. of ar. amines from phenols. F. e. s. R. Bayles et al., Synthesis 1977, 33, 31. 

Dispersion energy maps of benzene and N-methyl propanamide with neon as a probe. The SAPT(DFT) dispersion energy is displayed using an absolute scale inkJ mol". The model... 

Methyl-2-(o-phenylazopbenoxy)propanamide (Chart 9). Cleaved by reduction. 

Chemical Name 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl] -propanamide Common Name Niftolid... 

A -methyl-9,10-ethanoanthracene-9(10ll)-propanamide (C20H21NO 23716-34-9) see Maprotiline [liJ-[ltt,5a,6(7J )]]-a-(l-methylethenyl)-7-oxo-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene-6-acetic acid diphe-nylmethyl ester... 

Diethyl ether, methyl n-propyl ether, diethylamine, N-methyl-1 -propanamine, acetone, allyl alcohol, dimethylformamide, propanamide, 2-methylpropan-amide, 2,2-dimethylpropanamide, benzamide, dichloromethane, toluene, ethyl N-acetyl-glycinate, -alaninate, -methioninate, and -aspartate, ethyl acetate, tetrahydrofuran... 

A few modem nitrovasodilators have been designed and developed to improve pharmacokinetic properties. Two examples discussed below are (6-chloropyridin-2-yl)methyl nitrate and trans-2-amino-2-methyl-./V-[4-(nitro-oxy)cyclohexyl]propanamide. 

V-Methyl-2-methyl-3-(benzotriazol-l-yl)propanamide (631), on treatment with two equivalents of butyllithium, forms a dianion that reacts with alkyl and benzyl halides, aldehydes, and ketones to give monosubstituted products (632) (Scheme 124). With ethyl / -toluate, however, a lactam (634) is formed. The alkylated derivatives (632) eliminate benzotriazole upon treatment with NaOEt to afford trisubstituted a,)8-unsaturated amides (633) <93JHC1261>. 

When treated with a strong base such as butyllithium or potassium tert-butoxide, 2-isocyano-tV[(S)-l-phenylethyl]propanamide (1) forms an enolate 2 which is not alkylated at low temperatures. Instead it rearranges on warming and cyclizes to give the enolate of 3,5-dihydro-5-methyl-3-[(,3 )-1-phenylctbylJ-4//-imidazol-4-onc (3) which can be alkylated with benzylic halides with excellent diastereoselectivities4,13. 3-Halopropenes or haloalkanes give much lower diastereoselectivities. 

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