ChemicalBook CAS DataBase List (S)-2-(BOC-AMINO)-3-(3-HYDROXYPHENYL)PROPIONIC ACID METHYL ESTER

(S)-2-(BOC-AMINO)-3-(3-HYDROXYPHENYL)PROPIONIC ACID METHYL ESTER synthesis

8synthesis methods

Product Name:(S)-2-(BOC-AMINO)-3-(3-HYDROXYPHENYL)PROPIONIC ACID METHYL ESTER
CAS Number:900800-02-4
Molecular formula:C15H21NO5
Molecular Weight:295.33

24424-99-5 Synthesis

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L-Phenylalanine, 3-hydroxy-, Methyl ester

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(S)-2-(BOC-AMINO)-3-(3-HYDROXYPHENYL)PROPIONIC ACID METHYL ESTER

900800-02-4
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Yield: 0.48 g

Reaction Conditions:

with sodium hydrogencarbonate in methanol at 20; for 8 h;

Steps:

(S)-Methyl-2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate 11
To a solution of debenzylated ester 10 (1 g, 2.4 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1.1 mL, 14.6 mmol) slowly at 0 °C. After 3 h, reaction mixture was concentrated and washed with toluene (to remove the traces of TFA) to give Boc deprotected hydrazine. To the residue (0.5 g, 2.3 mmol) in MeOH (5 mL), activated W-2 Raney-Nickel (30 mg, pre-washed with anhydrous MeOH) and acetic acid (3 drops) were added. The reaction mixture was degassed and saturated with hydrogen (60 psi) for two times. The suspension was stirred at room temperature for 20 h, filtered through celite and the residue was washed thoroughly with MeOH (20 mL) and CH2Cl2 (10 mL). The combined filtrate was concentrated to afford the corresponding amine. To the stirred solution of the crude amine in MeOH (6.0 mL) were added (Boc)2O (0.8 g, 3.5 mmol) and NaHCO3 (until pH becomes basic). Reaction mixture was stirred at room temperature for 8 h. Solvent was evaporated under reduced pressure and the residue was purified by column chromatography (20% ethyl acetate/hexane) to furnish Boc-protected amine 11 as a white solid (0.48 g, 67% over three steps). M.P: 61-62 °C. [α]20D : +37.1 (c = 1.0, CHCl3). IR (KBr): νmax = 3376, 2980, 1744, 1684, 1593, 1515, 1368, 1163, 1059, 772, 698 cm-1. 1H NMR (CDCl3, 500 MHz): δ 7.15 (t, J = 7.7 Hz, 1H), 6.74-6.70 (dd, J = 7.7, 1.9 Hz, 1H), 6.67 (d, J = 7.7 Hz, 1H), 6.64-6.62 (m, 1H), 5.02 (d, J = 7.7 Hz, 1H), 4.61-4.54 (m, 1H), 3.71 (s, 3H), 3.09-3.02 (dd, J = 13.8, 5.6 Hz, 1H), 3.01-2.94 (dd, J = 13.5, 6.7 Hz, 1H), 1.42 (s, 9H) ppm. 13C NMR (CDCl3, 75 MHz): δ 172.5, 156.2, 155.4, 137.4, 129.6, 121.0, 116.1, 114.1, 80.3, 54.3, 52.2, 38.0, 28.2 ppm. HRMS (ESI): calcd. for C15H21NO5Na [M+Na]+ 318.1311; found 318.1307.

References:

Radhika, Laghuvarapu;Chandrasekhar, Srivari [Synthetic Communications,2014,vol. 44,# 24,p. 3602 - 3609] Location in patent:supporting information