Methyl 3-hydroxypropionate

CoSANSE = [bis(salicylidene-N-(methyl-3>hydroxypropionate))] Co Punniyamurthy, T. Iqbal. J. Tetrahedron Lett., 1994, 35, 4007... 

Methanolysis of 0-propiolactone with a trace of hydroxide catalyst gives a good yield of methyl 3 -hydroxypropionic acid, but with an equimolecular quantity of sodium methoxide the product is sodium 3-methoxypropionate (equation 48) (64hc(19-2)729). 

Forschner TC, Powell JB, Slaugh LH, Weider PR (2000) Process and catalysts for preparing 1,3-propanediol from methyl 3-hydroxypropionate. WO 2000/018712... 

The synthesis of the C1-C6 subunit started with the a-chiral ethylketone 73 [65], prepared from the commercially available methyl (S)-2-methyl-3-hydroxypropionate 1 in three steps. Enolization of 73 by... 

Related Reagents. 4-Cyanothiolan-3-one Ethyl Aceto-acetate Ethyl Acrylate Methyl 3-(Dimethylamino)propionate Methyl 3-Hydroxypropionate. 

Ethyl-2-methyl-3-hydroxypropionic acid 2-Ethyl-2-methyl-3-aminopropionic acid Al-Isobutyrylethylene amine V-Isopropyl-3-aminopropionic acid... 

P-Hydroxy acids lose water, especially in the presence of an acid catalyst, to give a,P-unsaturated acids, and frequendy P,y-unsaturated acids. P-Hydroxy acids do not form lactones readily because of the difficulty of four-membered ring formation. The simplest P-lactone, P-propiolactone, can be made from ketene and formaldehyde in the presence of methyl borate but not from P-hydroxypropionic acid. P-Propiolactone [57-57-8] is a usehil intermediate for organic synthesis but caution should be exercised when handling this lactone because it is a known carcinogen. 

Ethyl l-iodopropionate,/from ethyl 1-hydroxypropionate, methyl iodide, and triphenyl phosphite, Al, 47 Ethyl 4-methyl-E-4,8-non-... 

In our first attempt to bind linker-modified bis(pyrazol-l-yl)acetic acids to a solid phase we used Merrifield resin, which is one of the most popular solid phase supports. Since Merrifield polymer was designed to bind carboxylic acids, we used the ester methyl 2,2-bis(3,5-dimethylpyrazol-l-yl)-3-hydroxypropionate (52) instead of the 2,2-bis(3,5-dimethylpyrazol-l-yl)-3-hydroxypropionic acid (49). 

Triethylamine (4.8 ml, 34.4 mmol) is added to a stirred solution of methyl (2R,3S)-phenylisoserinate (7.26 g, 31.3 mmol) in methylene chloride (80 ml) at 0°C. To this slurry of is added trimethylsilyl chloride (4.4 ml, 34.7 mmol). Additional methylene chloride (45 ml) is added. The mixture is cooled to -65°C and triethylamine (9.8 ml, 70.3 mmol) is added. p-Nitrophenylsulfonyl chloride (6.93 g, 31.3 mmol) is added. The reaction rate is too slow at -65°C so the temperature is gradually raised to 0°C. Hydrogen fluoride (10% aqueous, 5 equivalents) is added. The aqueous phase is separated from the organic (methylene chloride) phase and methanol is added to the organic phase. The methylene chloride is removed under reduced pressure and the methyl (2R,3S)-3-(4-nitrobenzenesulfonamido)-3-phenyl-2-hydroxypropionate is obtained, melting point 187-189°C. 

Benzaldehyde dimethylacetal (200 pi, 1.33 mmol) and a catalytic amount of p-toluenesulfonic acid (37 mg) are added to methyl (2R,3S)-3-(4-nitrobenzenesulfonamido)-3-phenyl-2-hydroxypropionate (315 mg, 0.83 mmol) in toluene 5 ml. The mixture is heated at 100°C under reduced pressure (15 mm mercury) with no condenser. After 1 h the crude reaction mixture is diluted with ethyl acetate and washed with water (2 times). After drying the organic layer over magnesium sulfate the crude material is purified by column chormatography (silica gel eluting with ethyl acetate/cyclohexane, 35/65) to give the (2S,4S,5R)-2,4-diphenyl-3-(4-nitrobenzenesulfonamido)-5-methoxycarbonyl-l,3-oxazolidine, melting point 118°-120°C. 

The cyanohydrin synthesis of a-hydroxy acids is very often carried out without isolation or purification of the cyanohydrins. The various techniques for the preparation of the cyanohydrins are discussed elsewhere (method 390). Hydrolysis to the a-hydroxy acids is usually effected by heating with concentrated hydrochloric acid. Excellent directions are given for mandelic acid (52% over-all from benzaldehyde), a-methyl-a-hydroxybutyric acid (65% from methyl ethyl ketone), and eighteen dialkyl- and alkylphenyl-glycolic acids (60-80%). Sodium hydroxide solution is used in the preparation of /S-hydroxypropionic acid from the /S-hydroxy nitrile (80%). ... 

Lantibiotics contain several unusual amino acids, including the thioether lanthionine (Lan) hnkage and its methyl substituted analog methyUanthionine (MeLan) (Fig. la) that unifies all members of the class and accounts for their family name. In addition to Lan, lantibiotics commonly contain 2,3-dehydroalanine (Dha) and (Z)-2,3-dehydrobutyrine (Dhb). In all, no less than 15 different posttranslational modifications have been documented in lantibiotics (for a selection see Fig. la), and up to 58% of their amino acids are modified. These extensive structmal alterations overcome the constraints imposed by the use of 20 amino acids in ribosomally synthesized peptides. Some less common, posttranslationally crafted residues in lantibiotics are fS-hydroxy aspartate, lysinoalanine, aminovinyl cysteine (AviCys), D-alanine, 2-oxobutyrate, 2-oxopropionate, and 2-hydroxypropionate. The presence of these unusual residues is thought to be important for the biological activity of lantibiotics. 

Propionic acidaemia (ketonic hyper- Propionic, 3-hydroxypropionic, 2-methyl-... 

Figure 7.2.1. Cellulose pyrolysate obtained at 59CP C and trimethylsilylated. The separation was done on a methyl silicone with 5% phenyl silicone type column. 1 1,2-dihydroxyethane, 2 2-hydroxypropionic (lactic) acid, 3 hydroxy acetic (glycolic) acid, 4 turanmethanol, 5 peak from silylation reagents, 6 1,3-dihydroxypropanone, 7 1,4-dioxane-2,5-diol, 8 1,3-dioxolane-4,5-diol, 9 1,3-dihydroxybenzene, 10 2-methyl-1,4-dioxane-2,5-diol, 11 1,4-dihydroxybenzene, 12 3-hydroxy-2-(hydroxymethyl)-2-cyclopenten-1-one, 13 2-hydroxy-5-(hydroxymethyl)-4(H)-pyran-4-one, 14 1,2,3-trihydroxybenzene, 15 internal standard, 16 an anhydrosugar, 17 levoglucosan (1,6-anhydro-p-D-glucopyranose), 18 a monosaccharide, 19 an anhydrosugar, 20 an anhydrosugar, 21 1.6-anhydro-P-D-glucofuranose .

Finanz New Method of Synthesis of Ethyl Esters and Methyl Amides of 3-Phenyl-3-(4-Pyridyl)-3-Hydroxypropionic Acid and 3-Phenyl-3-(2-Pyridyl)-3-Hydroxypropionic Acid 1968 GB 1,106,517... 

AI3-00584 DL-Methyl lactate EINECS 208-930-0 EINECS 218-449-8 HSDB 5687 2-Hydroxypropanoic acid methyl ester Lactic acid, methyl ester Methyl 2-hydroxypropanoate Methyl a-hydroxypropionate ( )-Methyl 2-hydroxypropanoate Methyl lactate ( )-Methyl lactate NSC 406248 Propanoic acid, 2-hydroxy-, methyl ester. Colorless liquid bp = 144-145 d = 1.09 soluble in EtOH, Et20. 

Chloroflexus aurantiacus fixes carbon using the 3-hydroxypropionate pathway (Strauss and Fuchs 1993). Remarkably, it is known also to produce its isoprenoids from acetate via the MVA pathway (Rieder et al. 1998). Van der Meer et al. (2001b) point out that, if the same pool of acetate is used to produce the -alkyl lipids, the isotopic compositions at the methyl and carboxyl positions of the acetate groups used in biosynthesis can be calculated (e.g. there are 12 methyl and 8 carboxyl carbons in the C20 isoprenoid and 8 of each in the Cie fatty acid). The fractionations reported in Table 5 then indicate that the carboxyl carbon is enriched in relative to the methyl carbon by 40%o The pathways of carbon flow in C. aurantiacus are very incompletely known and the branch points potentially responsible for such a large fractionation cannot be identified. 

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