2-methoxy-2- propionic acid

R.3S) -3-tert-butoxy-carbonylomino-3-phenyl-2-(2,2,2-trichloroethoxy-methoxy)propionic acid (XIX)... 

Write equations for the reactions which take place when the ethyl ester a-methoxy-propionic acid is (a) boiled with a solution of sodium hydroxide and (6) when it is heated with a solution of hydriodic acid. 

Dysinosins are alkaloid tripeptides with very unusual a-substituted acid residues, including 5,6-dyhydroxyoctahydroindole-2-carboxylic acid and 3-sulfonic-2-methoxy propionic acid, as well as the basic moiety 2-aminoethyl-(l-N-amidino-A-3-pyrroline). Among them, dysinosin A (170), isolated from an identified sponge belonging to the family Dysideidae, inhibited factor Vila with a Ki of 108 nM and thrombin with a of 452 nM [159],... 

C5H10O3 3-methoxy-propionic acid methyl ester 3852-09-3... 

C7H14O3 3-methoxy-propionic acid propyl ester 5349-56-4... 

C9H18O3 3-methoxy-propionic acid pentyl ester 10500-16-0... 

C14H28O3 3-methoxy-propionic acid decyl ester ... 

In 1909, Thiele and Landers reported the synthesis of p- (3-methoxy-isoxazol-5-yl)-propionic acid (77), from the corresponding chloride or bromide (76). In 1961, a similar reaction was reported for 3-chloro-5-arylisoxazoles, enabling the synthesis of 3-hydroxy-5-phenyl-... 

Chemical Name (+)-6-methoxy-a-methyl-2-naphthaleneacetic acid Common Name d-2-(6-methoxy-2-naphthyl)propionic acid Structural Formula ... 

Compound (+ )-(53) has been made from one of the diastereomers of the (—)-menthyl ester of 3-(p-anisylmethyl-l-naphthylstannyl)propionic acid, (54) ([a]p°° — 24) which could be obtained from the mixture of diastereomers because it is much less soluble in -pentane at low temperature than the other one. Their separation could be followed by NMR, both diastereomers differing by the position of their methoxy signal. The pure less soluble diastereomer (54) reacts with methylmagnesium iodide to give a tetraorganotin compound containing only one chiral center, the asymmetric tin atom 36> 87>. 

It may be mentioned that the diastereomers of the analogous compound bearing a hydrogen atom instead of the methoxy group, the (—-)-methyl esters of 3-(methyl-l-naphthylphenylstannyl)propionic acid, could not be separated analogously. Moreover, NMR spectroscopy could not be used as in the former case to determine the diastereomeric ratio. 

Monsanto [117] has developed a way to electrosynthesize by reductive carboxylation the optically active precursor to Naproxen, (S)-2-(6 -methoxy-2 -naphthyl)propionic acid, a drug used to treat arthritis. A more economical route was needed since the US patent expires in 1993 while the market is growing. The electrochemical process is said to cut manufacturing costs by over 50%. Since it uses CO 2 instead of the hazardous HCN used in conventional synthesis, it is also safer. 

Electrochemistry offers new routes to the production of several commercially relevant a-arylpropionic acids, used as non-steroidal anti-inflammatory agents (NSAI) [178,182]. A preparative method based on sacrificial Al-electrodes has been set up for the electrocarboxylation of ketones [117,183-187] and successfully applied to the electrocarboxylation of aldehydes, which failed with conventional systems. The electrocarboxylation of 6-methoxy-acetonaphthone to 2-hydroxy-2-(6-methoxynaphthyl)propionic acid, followed by chemical hydrogenation to 2-(6-methoxynaphthyl)-2-propionic acid - one of the most active NSAI acids - has been developed up to the pilot stage [184,186],... 

A thorough study on the ion-exchange mechanism and the effect of distinct counterions in this PO mode was recently presented by Gyimesi-Forras et al. [41]. A large variety of distinct acid additives to methanol, acetonitrile, and tetrahydrofuran (Table 1.1) (without any base added) was investigated in view of the stoichiometric displacement model and their effect on the enantiomer separation of 2-methoxy-2-(l-naphthyl)propionic acid. The stoichiometric displacement model (Equation 1.1) was obeyed also in the PO mode, as revealed by linear plots of log k vs. acid concentration. The slopes and intercepts along with the concentration ranges used with the distinct competitor acids are summarized in Table 1.1. 

Influence of Acid Additives on Retention Characteristics of 2-Methoxy-2-(1-Naphthyl)Propionic Acid on a 0-9-(tert-ButylcarbamoyOQuinine CSP as Assessed by the Characteristic Parameters of the Stoichiometric Displacement Model (Slopes and Interc ... 

FIGURE 1.20 X-ray crystal structure of the more stable complex between 0-9-(tert-butylcarbamoyl)quinine and (5)-2-methoxy-2-(l-naphthyl)propionic acid (two distinct perspectives). (Reprinted from K. Akasaka et al., Chirality, 17 544 (2005). With permission.)... 

Methoxy-2-(l-naphthyl)propionic acid, 2-methoxy-2-(l-naphthyl)acetic... 

Structural information on aromatic donor molecule binding was obtained initially by using H NMR relaxation measurements to give distances from the heme iron atom to protons of the bound molecule. For example, indole-3-propionic acid, a structural homologue of the plant hormone indole-3-acetic acid, was found to bind approximately 9-10 A from the heme iron atom and at a particular angle to the heme plane (234). The disadvantage of this method is that the orientation with respect to the polypeptide chain cannot be defined. Other donor molecules examined include 4-methylphenol (p-cresol) (235), 3-hydroxyphenol (resorcinol), 2-methoxy-4-methylphenol and benzhydroxamic acid (236), methyl 2-pyridyl sulfide and methylp-tolyl sulfide (237), and L-tyrosine and D-tyrosine (238). Distance constraints of between 8.4 and 12.0 A have been reported (235-238). Aromatic donor proton to heme iron distances of 6 A reported earlier for aminotriazole and 3-hydroxyphenol (resorcinol) are too short because of an inappropriate estimate of the molecular correlation time (239), a parameter required for the calculations. Distance information for a series of aromatic phenols and amines bound to Mn(III)-substituted HRP C has been published (240). 

Torchilin et al. synthesized an iodine-containing amphiphilic block-copolymer consisting of iodine-substituted poly-L-lysine which is able to form micelles in aqueous solution [37]. The two components of the block-copolymer were methoxy-poly(ethylene glycol) propionic acid (MPEG-PA) with a molecular weight of 12 kDa and poly[ ,M-(2,3,5-triiodobenzoyl)]-L-lysine. The particle size of the micelles was approx. 80 nm, and the iodine concentration was 20 mg mL . Biodistribution studies in rats showed significant and prolonged enhancement of the aorta, the liver and spleen. 

The phenols (no. 30a, 30b, 32) are used as reactants to synthesize several of the company s products, including the benzotriazoles. The 2-chloro-4,6-bls-isopropylam-ino-s-triazine (no. 13) are herbicides the chloro compound is used to control weeds and grass in corn and in milo, and the methoxy compound is used for general plant control. Several esters of 3-(3 ,5 -di-t-butyl-4 -hydroxyphenyl) propionic acid were identified, the most abundant being the octadecyl and methyl esters. 

Naproxene Naproxene, 2-(6-methoxy-2-naphthyl)-propionic acid (3.2.15) can be synthesized by the methods of synthesis described for ibuprofen as well as by the methods of fenoprofen (3.2.21) and ketoprofen (3.2.27) synthesis that will be described below from 2-acetyl or 2-chloromethyl-6-methoxynaphthaline [99-101]. 

Synthesis of racemic naproxene Friedel-Crafts acylation (aluminum chloride - nitrobenzene) of p-naphthol methyl ether affords 2-acetyl-6-methoxy naphthalene, which, when treated with either dimethyl sulfonium or dimethylsulfoxonium methylide, gives 2-(6-methoxynaphthalen-2-yl)propylene oxide. Treatment of the latter with boron trifluoride etherate in tetrahydrofuran gives 2-(6-methoxynaphthalen-2-yl)propionaldehyde, which is oxidized using Jones reagent (4 M chromic acid) to yield the racemic 2-(6-methoxynaphthalen-2-yl)propionic acid. 

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