ChemicalBook CAS DataBase List Fmoc-Phe-OH

Fmoc-Phe-OH synthesis

6synthesis methods

Product Name:Fmoc-Phe-OH
CAS Number:35661-40-6
Molecular formula:C24H21NO4
Molecular Weight:387.43

63-91-2 Synthesis

63-91-2
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28920-43-6
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35661-40-6
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Yield:35661-40-6 82%

Reaction Conditions:

Stage #1:L-phenylalanine;(fluorenylmethoxy)carbonyl chloride with sodium carbonate in 1,4-dioxane;water at 0 - 20; for 22 h;
Stage #2: with hydrogenchloride in water

Steps:

4.2.3. 9-Fluorenylmethoxycarbonyl-l-phenylalanine (12)
To a solution of l-phenylalanine 11 (0.96 g, 5.81 mmol) in dioxane (7.5 ml) and 10% Na₂CO₃ aq (15 ml) was added Fmoc-Cl (1.50 g, 5.79 mmol) in dioxane (15 ml). The reaction mixture was stirred at 0 °C for 4 h and room temperature for 18 h, added water (400 ml) and washed with Et₂O (2×200 ml). The aqueous layer was acidified with cHCl, filtered and dried to yield Fmoc-l-Phe 12 (1.91 g, 4.93 mmol, 82%) as a white powder; Mp 182-183 °C; ¹H NMR (400 MHz, CDCl₃) δ_H 7.78-7.14 (13H, m), 5.18 (1H, d, J=8.2 Hz), 4.70 (1H, m), 4.45 (1H, m), 4.37 (1H, m), 4.21 (1H, m), 3.20 (1H, m), 3.14 (1H, m).

References:

Ishiyama, Haruaki;Yoshizawa, Kazuaki;Kobayashi, Jun'ichi [Tetrahedron,2012,vol. 68,# 31,p. 6186 - 6192] Location in patent:experimental part

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