| Identification | More | [Name]
H-D-TYR-OME HCL | [CAS]
3728-20-9 | [Synonyms]
D-TYROSINE METHYL ESTER HYDROCHLORIDE
D-TYROSINE-OME HCL
H-D-TYR-OME HCL
METHYL D-TYROSINATE HYDROCHLORIDE
H-D-Tyr-OMe·HCI
D-Tyrosine Methyl Ester HCl
H-D-Try-OMe-HCl | [EINECS(EC#)]
223-084-2 | [Molecular Formula]
C10H14ClNO3 | [MDL Number]
MFCD00066124 | [Molecular Weight]
231.68 | [MOL File]
3728-20-9.mol |
| Hazard Information | Back Directory | [Chemical Properties]
Crystalline | [Uses]
D-Tyrosine methyl ester hydrochloride is an intermediate in the synthesis of oxybutynin chloride (O868525), an inhibitor of proliferation and supresses gene expression in bladder smooth muscle cells. | [Synthesis]
General procedure for the synthesis of methyl (R)-2-amino-3-(4-hydroxyphenyl)propanoate hydrochloride from methanol and D-tyrosine: (2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid (49) (1.07 g, 5.9 mmol) was dissolved in methanol, and the reaction was completed to give methyl (2R)-2-amino-3-(4-hydroxyphenyl)propanoate (50) . The product characterization data were as follows: melting point 176°C (literature values in agreement); 1H NMR (DMSO-d6) δ: 6.82 (d, J = 8.4 Hz, 2H, ArH3' and ArH5'), 4.13 (t, J = 6.9 Hz, 1H, H2), 3.83 (s, 3H, OCH3), 3.22 (dd, J = 6.0, 14.4 Hz. 1H, 3Ha), 3.12 (dd, J = 6.9, 14.7 Hz, 1H, 3Hb). Mass spectrum (chemical ionization, positive ion mode) m/z: 196 (100%) [M+]. High Resolution Mass Spectrometry (HRMS) calculated value of C10H14NO3: 196.0974, measured value: 196.0985. | [References]
[1] Organic Letters, 2002, vol. 4, # 2, p. 265 - 267
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 4, p. 636 - 643
[3] Patent: WO2006/74501, 2006, A1. Location in patent: Page/Page column 152
[4] Tetrahedron, 2008, vol. 64, # 49, p. 11270 - 11290
[5] Organic and Biomolecular Chemistry, 2005, vol. 3, # 7, p. 1233 - 1239 |
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