ChemicalBook CAS DataBase List Boc-N-methyl-L-leucine

Boc-N-methyl-L-leucine synthesis

8synthesis methods

Product Name:Boc-N-methyl-L-leucine
CAS Number:53363-89-6
Molecular formula:C12H23NO4
Molecular Weight:245.32

13139-15-6
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$7.00/5g

74-88-4
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$15.00/10g

53363-89-6
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$9.00/250mg

Yield:53363-89-6 98%

Reaction Conditions:

Stage #1: N-tert-butoxycarbonyl-L-leucinewith sodium hydride in tetrahydrofuran;mineral oil at 0; for 0.5 h;Inert atmosphere;
Stage #2: iodomethane in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 4.5 h;Inert atmosphere;

Steps:

To a solution of Boc-L-Leu (5.0 g, 21.6mmol) in THF (73 mL) wasadded NaH (60% dispersion in mineral oil, 10.0 g, 0.13 mol) inportions at 0 oC. After stirring at 0 oC for 30 min, MeI (4.1 mL,66.0 mmol) and DMF (3.7 mL) were successively added. Thereaction was stirred for 30 min at 0 oC and additional 4 h atrt, until it was quenchedwith H2O (50 mL). The mixture was extracted by EtOAc (2×100 mL). The aqueoussolution was then acidified with 10% aqueous KHSO4 solution to pH 5 and extractedwith ethyl acetate. The combined EtOAc extracts were washed with 5% Na2S2O4solution and brine, and dried over Na2SO4, filtered and evaporated to give 13 (5.2 g,98% yield) as a colorless oil.

References:

He, Wei;Qiu, Hai-Bo;Chen, Yi-Jie;Xi, Jie;Yao, Zhu-Jun [Tetrahedron Letters,2014,vol. 55,# 44,p. 6109 - 6112] Location in patent:supporting information

13139-15-6
439 suppliers
$7.00/5g