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ChemicalBook CAS DataBase List Boc-N-Me-Val-OH
45170-31-8

Boc-N-Me-Val-OH synthesis

10synthesis methods
To a solution of N-BOC-valine 1 (217 mg, 1 mmol) and iodomethane(1.42 g, 10 mmol) in anhydrous tetrahydrofuran (THF,20 mL) was added neat sodium hydride (240 mg, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was then quenched with water (30 mL). The reaction mixture was extracted with ethyl acetate (EtOAc, 2 15 mL) and the aqueous solution was acidified to pH 3, after which it was extracted with EtOAc (3 20 mL). The combined organic phase was dried over anhydrous Na2SO4 and evaporated to afford the corresponding Boc-N-Me-Val-OH (thick colorless oil), 99% yield.
Boc-N-Me-Val-OH
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Yield:45170-31-8 99%

Reaction Conditions:

with sodium hydride in tetrahydrofuran at 20; for 24 h;

Steps:



To a solution of N-BOC-valine 1 (217 mg, 1 mmol) and iodomethane(1.42 g, 10 mmol) in anhydrous tetrahydrofuran (THF,20 mL) was added neat sodium hydride (240 mg, 10 mmol). Thereaction mixture was stirred at room temperature for 24 h. The mixture was then quenched with water (30 mL). The reaction mixturewas extracted with ethyl acetate (EtOAc, 2 15 mL) and theaqueous solution was acidified to pH 3, after which it wasextracted with EtOAc (3 20 mL). The combined organic phasewas dried over anhydrous Na2SO4 and evaporated to afford the corresponding N-methylated product 2 (thick colorless oil), 99%yield.

References:

Ge, Xin;Qian, Chao;Chen, Xinzhi [Tetrahedron Asymmetry,2014,vol. 25,# 22,p. 1450 - 1455]

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