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ChemicalBook CAS DataBase List H-PHE-PYRROLIDIDE

H-PHE-PYRROLIDIDE synthesis

5synthesis methods
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Yield:56414-89-2 78%

Reaction Conditions:

with 4-methyl-morpholine;(3,3,3-trifluoropropyl)methyldichlorosilane in acetonitrile at 40; for 18 h;

Steps:

General procedure for syntheses of amino acid amides 4aa4am shown in Table 3

General procedure: L-Phenylalanine 1a (33.0 mg, 0.2 mmol) and imidazole (68.1 mg, 1 mmol) were suspendedin dry CH3CN (1 mL), and dichloro(methyl)(3,3,3-trifluoropropyl)silane 3b (82.4 L, 0.5mmol) and isopropylamine 2a (120.8 L, 1.4 mmol) were added at 0 C. The reaction mixturewas stirred for 18 h at 40 C and then quenched with aqueous solution of NaHCO3/KF. Thereaction mixture was extracted with ethyl acetate (×2), and the combined organic layer wasdried over Na2SO4 and concentrated in vacuo. Purification of the crude product by flashchromatography on silica gel (DCM/MeOH/triethylamine = 90/10/0.1) provided (S)-2-amino-N-isopropyl-3-phenylpropanamide 4aa (32.3 mg, 78%).

References:

Nobuta, Tomoya;Morishita, Honoka;Suto, Yutaka;Yamagiwa, Noriyuki [Synlett,2022,vol. 33,# 15,p. 1563 - 1569] Location in patent:supporting information

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