ChemicalBook CAS DataBase List Boc-Aib-OH

Boc-Aib-OH synthesis

14synthesis methods

Product Name:Boc-Aib-OH
CAS Number:30992-29-1
Molecular formula:C9H17NO4
Molecular Weight:203.24

24424-99-5 Synthesis

24424-99-5
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62-57-7
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30992-29-1
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$6.00/5g

Yield:30992-29-1 90%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water at 20; for 16 h;Cooling with ice;

Steps:

2-(1-(((tert-butoxycarbonyl) amino) methyl) cyclohexyl) aceticacid (3a)
General procedure: To a stirred solution of 2-(1-(aminomethyl) cyclohexyl)acetic acid 2a (2g, 11.68 mmol, 1equiv.) in 1, 4-dioxane (20 mL) atice temperature, aq. NaOH (560.57mg, 14.02 mmol, 1.2 equiv,dissolved in 10 mL water) was added followed by addition of ditert-butyl dicarbonate (5.10 gm, 23.36mmol, 2 equiv.) in 1,4-dioxane (5mL). The reaction mixture was stirred at room temperature for 16 h. The resulting suspension was concentrated in vacuo and the residuewas dissolved in water (10-15mL) and washed by ethyl acetate (15mL x 2). The resultingaqueous layer was acidified using dilute KHSO4 solution, followed by extraction withethyl acetate (30 mL x 3), dried (Na2SO4) and concentrated in vacuo to afford 3a as awhite solid, which was carried forward for the next reaction. Yield: 3.04g, 95%.

References:

Dangi, Abha;Marelli, Udaya Kiran;Meena, Chhuttan L.;Reichart, Florian;Sanjayan, Gangadhar J.;Singh, Dharmendra;Zahler, Stefan;Weinmüller, Michael [Bioorganic and medicinal chemistry letters,2020] Location in patent:supporting information

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