ChemicalBook CAS DataBase List methyl (2S)-2,6-bis({[(tert-butoxy)carbonyl]amino})hexanoate

methyl (2S)-2,6-bis({[(tert-butoxy)carbonyl]amino})hexanoate synthesis

9synthesis methods

Product Name:methyl (2S)-2,6-bis({[(tert-butoxy)carbonyl]amino})hexanoate
CAS Number:2483-48-9
Molecular formula:C17H32N2O6
Molecular Weight:360.45

2483-46-7 Synthesis

2483-46-7
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methyl (2S)-2,6-bis({[(tert-butoxy)carbonyl]amino})hexanoate

2483-48-9
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Yield:2483-48-9 97%

Reaction Conditions:

with potassium carbonate in ethyl acetate;N,N-dimethyl-formamide at 10 - 20; for 5 h;Inert atmosphere;

Steps:

2 Boc-L-Lys(Boc)-OMe

Example 2
Boc-L-Lys(Boc)-OMe
A 1 L three-neck flask equipped with addition funnel, nitrogen inlet, thermometer and mechanical stirrer was charged with a solution of Boc-L-Lys(Boc)-OH (59.37 g, 161 mmol, 94 wt % in EtOAc) in N,N-dimethylformamide (anhydrous) (300 mL).
Whilst stirring, potassium carbonate (24.5 g, 177 mmol) was added, and the resulting suspension was cooled on an ice bath to an internal temperature of +10° C. Iodomethane (34.3 g, 242 mmol, 15.04 mL) was added dropwise over 30 min via the addition funnel, while keeping the internal temperature <20° C.
The ice bath was removed and the reaction mixture was allowed to reach room temperature. TLC indicated complete consumption of the starting material after 4.5 h of stirring at room temperature.
All volatiles were removed in vacuo, the resulting white slurry solidified on standing, and it was stored at -20° C. overnight.
The resultant material was taken up in water (1 L) and sat'd. NaHCO₃ (0.5 L), and then extracted with EtOAc (3*500 mL).
The combined organic phases were washed with dilute brine (2*200 mL), brine (2*100 mL), then dried over Na₂SO₄ and concentrated.
After stripping with heptane (2*200 mL), the title compound was isolated as a white solid (57.08 g, 97% yield).
¹H-NMR (CDCl₃):
In agreement with structure.
LCMS (NQAD detection):
Purity >99%, mass in agreement with molecular formula (pos. m/z=361 [M+1]⁺, 383 [M+Na]⁺).
Specific rotation: [α]_D²²=6.38° (c=1.72, CHCl₃).