(+)-Methyl lactate

Colorless to light yellow liquiChEBI: A methyl lactate that has R configuration.

Methyl (R)-lactate is a methyl lactate that has R configuration. It derives from a (R)-lactic acid. It is an enantiomer of a methyl (S)-lactate.

A standard 500‐μL hydrolytic reaction system containing140 μg purified esterase PHE14, 50 mmol/L substrate (racemicmethyl lactate) and 50 mmol/L phosphate buffer (pH 7.5) wasincubated at 37 °C for 1 h. After the completion of the enzymaticreaction, reaction samples were extracted with an equalvolume of ethyl acetate and the organic phase was further analyzedto evaluate the enzymatic resolution of (±)‐methyl lactate.Test Example 5Production of Optically Active 2-Hydroxy Ester Using Various Types of Racemic 2-Hydroxy Ester (3) As shown in the above reaction scheme, to diethyl ether (0.2 M) containing 0.6 equivalents of pivalic acid anhydride and 0.5 equivalents of diphenylacetic acid were added 1.2 equivalents of diisopropyl ethylamine, 5percent by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of a racemic 2-hydroxy ester in diethyl ether at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. After the organic layers were admixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active 2-hydroxy ester. The results are shown in Table 5. TABLE 5 Yield [percent] Methyl pyruvate (51 mg; 0.50 mmol) was dissolved in a reaction vessel in anhydrous THF (3.0 mL) and degassed with argon for 15 minutes. Bis(1, 5-cycloocta-diene)rhodium trifluoromethanesulfonate (2.3 mg; 5 μmol; 0.01 equiv) and ligand 4a from (3.7 mg; 6 μmol; 0.012 equiv) were combined and argon-degassed anhydrous THF (2.0 mL) was added. This solution was stirred at 25° C. under argon for 15 minutes and then added to the solution of 2-acetamidocinnamic acid. The resulting solution was then flushed with hydrogen and pressurized to 0.69-1.38 bars gauge (10-20 psig) hydrogen. The reaction mixture was stirred for 8 hours to afford 90.2percent conversion to methyl (R)-lactate with 88.2percent ee as determined by chiral GC analysis. The analytical properties of methyl lactate were identical to an authentic sample.Chiral GC [Cyclosil-B (JGeneral procedure: All catalytic reactions were carried out at 50 C in 25 mL ofmethanol solvent in a stainless steel autoclave reactorequipped with a gas inlet and outlet, pressure gauge, mechanicalstirrer and temperature controller thermocouple. The systemwas controlled by computerized software and an electronicmotherboard unit. For each reaction, 70 mg (0.1 mmol ofcatalytically active Pt metal) of solid catalyst and 100 mmol ofsubstrate were used. The catalytic hydrogenation reaction wascarried out under 5 MPa of hydrogen and the reaction time wasfixed at 2 h. At the end of the catalytic runs, the reaction mixturewas analyzed by GC and the conversion was calculated onthe basis of the areas of the starting material and product usingcalibration curve calculations.The hydrogenation reaction of methyl pyruvate was performed by the same method as in Example 38 except that the sulfonate catalyst was changed to Ru(OTf)[(S, S)-Tsdpen](p-cymene). As a result, (S)-methyl lactate with 33percent ee was produced in a yield of only 25percent.In a stainless steel autoclave, Cp*Ir(OTf)[(S, S)-Tsdpen] (1.7 mg, 2.0 μmol) was charged, followed by purging with argon. Then, 1 ml of methanol and methyl pyruvate (0.18 ml, 2.0 mmol) were charged, and the autoclave was pressurized with hydrogen, followed by ten times of purging. Then, hydrogen was charged to 30 atm to initiate reaction. After stirring at 50° C. for 15 hours, the reaction pressure was returned to normal pressure. General procedure: All catalytic reactions were carried out at 50 C in 25 mL ofmethanol solvent in a stainless steel autoclave reactorequipped with a gas inlet and outlet, pressure gauge, mechanicalstirrer and temperature controller thermocouple. The systemwas controlled by computerized software and an electronicmotherboard unit. For each reaction, 70 mg (0.1 mmol ofcatalytically active Pt metal) of solid catalyst and 100 mmol ofsubstrate were used. The catalytic hydrogenation reaction wascarried out under 5 MPa of hydrogen and the reaction time wasfixed at 2 h. At the end of the catalytic runs, the reaction mixturewas analyzed by GC and the conversion was calculated onthe basis of the areas of the starting material and product usingcalibration curve calculations.General procedure: Hydrogenation reaction was performed in a Picoclave GlassUster cyclone 075 BUCHI autoclave. A solution of the precursor and the modifier: 0.0304 g (1×10General procedure: was synthesized from corresponding from L-Lactic acid (20 g, 0.225 mole) (5) via diazotization using a reported procedure starting from Alanine (3).A standard 500‐μL hydrolytic reaction system containing140 μg purified esterase PHE14, 50 mmol/L substrate (racemicmethyl lactate) and 50 mmol/L phosphate buffer (pH 7.5) wasincubated at 37 °C for 1 h. After the completion of the enzymaticreaction, reaction samples were extracted with an equalvolume of ethyl acetate and the organic phase was further analyzedto evaluate the enzymatic resolution of (±)‐methyl lactate.

Molecular Weight:104.10
XLogP3:-0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:104.047344113
Monoisotopic Mass:104.047344113
Topological Polar Surface Area:46.5
Heavy Atom Count:7
Complexity:69.3
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes