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ChemicalBook CAS DataBase List Boc-Lys(Boc)-OH
2483-46-7

Boc-Lys(Boc)-OH synthesis

9synthesis methods
Di-tert-butyl dicarbonate

24424-99-5

L-Lysine hydrochloride

657-27-2

Boc-Lys(Boc)-OH

2483-46-7

The general procedure for the synthesis of (S)-2,6-di-Boc-aminohexanoic acid from di-tert-butyl dicarbonate and L-lysine hydrochloride was as follows: first, L-lysine hydrochloride was dissolved in 50 mL of a solvent mixture of 1,4-dioxane and water (1:1, v/v), and the pH was adjusted to 10-11 by the dropwise addition of 1 M NaOH solution Next, the pH of L-lysine hydrochloride (2.0 g) was adjusted to 10-11 by slow addition through the addition funnel. Di-tert-butyl dicarbonate (6.0 g) dissolved in 20 mL of dioxane. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently acidified with 4 M KHSO4 solution to pH=1-2. The acidified solution was extracted twice with ethyl acetate, the organic phases were combined and dried under reduced pressure to give a colorless liquid product in 100% yield.

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Yield:2483-46-7 100%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water at 20;

Steps:

16 Synthesis of Boc-lysine-Boc

To the solution of Lysine HCl salt in 50 ml 1,4-dioxane/H2O (1:1), 1M NaOH is added until pH reaches 10-11. Then Boc anhydride in dioxane (6.0 g in 20 ml dioxane) is added by an addition funnel. The resulting solution is stirred at room temperature overnight. The mixture is concentrated in vacuo and acidified by 4M KHSO4 until pH=1-2. Extract by Ethyl acetate twice and dried in vacuo. Colorless liquid is obtained and yielding is 100%

References:

US2014/127138,2014,A1 Location in patent:Paragraph 0321; 0322

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