D-Tyrosine, methyl ester, hydrochloride
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D-Tyrosine, methyl ester, hydrochloride
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CAS No:
3728-20-9
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Formula:
C10H13NO3.ClH
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Chemical Name:
D-Tyrosine, methyl ester, hydrochloride
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Synonyms:
D-Tyrosine,methyl ester,hydrochloride (1:1);Tyrosine,methyl ester,hydrochloride,D-;D-Tyrosine,methyl ester,hydrochloride;Methyl D-tyrosinate hydrochloride
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CAS No:
D-Tyrosine, methyl ester, hydrochloride Basic Attributes
231.68
231.066223
223-084-2
DTXSID40190732
2922509090
D-Tyrosine, methyl ester, hydrochloride Use and Manufacturing
Methyl (2fi)-2-amino-(4-hydroxyphenyl)-2-propanoate hydrochloride (50); To a solution of (2/?)-2-amino-3-(4-hydroxyphenyl)propanoic acid 49 (1.07 g, 5.9 mmol) in The resulting to yield the data in agreement Mp 176General procedure: The methyl-esterification reaction of L-phenylalanine.To a suspension of L-phenylalanine (1 g, 6.05 mmol, 1.0 equiv) inmethanol (25 mL) cooled to 0 C was added thionyl chloride(475 mL, 6.66 mmol, 1.5 equiv) slowly. After 10 min, the reactionmixture was heated to 75 C to reflux for 2 h. After completion(monitored by TLC), the solvent was removed in vacuo, and at thistime, a white solid was formed methyl L-phenylalaninate hydrochloride(1.23 g, quantitative yield).The L- tyrosine (110g, 0.607mol) was added to 500mL of methanol, cooled to 0 deg.] C, was added dropwise thionyl chloride(108.3g, 0.91mol). After the dropwise addition to naturally warm to room temperature and then the reaction was heated at reflux for 5h, TLC monitored the reaction was complete. It cooled to room temperature, filtered, the filter cake washed with 420mL of ethyl acetate with drying of 140.2 g of a white solid, a yield of 99.7percentStep 1(S). 1aniino2( 4hydroxypheny1)ethyI acetate hydrochloride To an icebath cooled MeOH (600 rnL)was added 78.S g SOCl (0662. mol, 1.2 eq) dropwise. After the addition, the solution was cooled to i0 °C and 100.0 g tyrosine (C. 552 mol, 1.0 eq) was added. The resulting solution was stilTed at 25 °C for 48 hrs, and TLC (FA) indicated the reaction was completed. The solution was concentrated to dryness to afford 129.0 g of the title compound.
Computed Properties
Molecular Weight:231.67
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:231.0662210
Monoisotopic Mass:231.0662210
Topological Polar Surface Area:72.6
Heavy Atom Count:15
Complexity:188
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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D-Tyrosine, methyl ester, hydrochloride
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