| Identification | Back Directory | [Name]
(S)-Isopropyl 2-amino-3-(4-hydroxyphenyl)propanoate | [CAS]
126173-94-2 | [Synonyms]
L-Tyr-Oipr.Hcl L-Tyrosine isopropyl ester L-Tyrosine, 1-methylethyl ester (S)-Isopropyl 2-amino-3-(4-hydroxyphenyl)propanoate Propan-2-YL (2S)-2-amino-3-(4-hydroxyphenyl)propanoate (S)-Isopropyl 2-amino-3-(4-hydroxyphenyl)propanoate USP/EP/BP (S)-isopropyl 2-amino-3-(4-hydroxyphenyl)propanoate hydrochloride | [Molecular Formula]
C12H17NO3 | [MOL File]
126173-94-2.mol | [Molecular Weight]
223.27 |
| Hazard Information | Back Directory | [Synthesis]
1. dissolve L-tyrosine (100 g, 552 mmol) in 2-propanol (1.00 L).
2. Concentrated sulfuric acid (60 mL) was added slowly and dropwise to the above solution.
3. The reaction mixture was stirred at 80 °C for 48 hours.
4. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure.
5. Saturated aqueous potassium bicarbonate was added to the concentrated residue with thorough stirring.
6. The solid product was collected by filtration.
7. The solid product was dried under reduced pressure to afford isopropyl (S)-2-amino-3-(4-hydroxyphenyl)propionate (129 g, 85% yield) as a white solid. 8.
8. Product characterization data: 1H NMR (CD3OD, 400 MHz): δ 7.01 (d, J = 8.0 Hz, 2H), 6.71 (d, J = 8.4 Hz, 2H), 4.96-4.90 (m, 1H), 3.62 (t, J = 6.8 Hz, 1H), 2.91-2.80 (m, 2H), 1.15 (d, J = 6.4 Hz, 6H). 6.4 Hz, 6H).MS (ESI) m/z 224 (M + H)+. | [References]
[1] Patent: US2015/51395, 2015, A1. Location in patent: Paragraph 0649-0650 [2] Journal of Pharmacy and Pharmacology, 1995, vol. 47, # 10, p. 861 - 869 [3] Journal of Natural Products, 2007, vol. 70, # 7, p. 1084 - 1088 [4] Patent: WO2004/101560, 2004, A1. Location in patent: Page 25 |
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