ChemicalBook CAS DataBase List N-Boc-N'-Cbz-L-lysine

N-Boc-N'-Cbz-L-lysine synthesis

13synthesis methods

Product Name:N-Boc-N'-Cbz-L-lysine
CAS Number:2389-45-9
Molecular formula:C19H28N2O6
Molecular Weight:380.44

13139-17-8

13734-28-6

2389-45-9

The general procedure for the synthesis of N-Boc-N'-Cbz-L-lysine from N-alpha-Boc-L-lysine and phenylmethoxycarbonylsuccinimide was as follows: to a mixed solution of (2S)-6-amino-2-(tert-butoxycarbonylamino)hexanoic acid (100.00 g, 406.01 mmol, 1.00 equiv) and NaHCO3 (102.33 g 1.22 mol, 3.00 eq.) in a mixed solution of THF (1000 mL) and water (1000 mL) was slowly added CbzOSu (101.19 g, 406.01 mmol, 1.00 eq.) at 0 °C. Subsequently, the reaction mixture was stirred at 30 °C for 16 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5-6 with 1N HCl and then extracted with ethyl acetate (600 mL x 3). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product (2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (142.00 g, 373.26 mmol, 91.9% yield) as a yellow oil.

13139-17-8
516 suppliers
$6.00/25g

13734-28-6
359 suppliers
$8.00/1g

2389-45-9
320 suppliers
$6.00/1g

Yield:2389-45-9 91.9%

Reaction Conditions:

with sodium hydrogencarbonate in tetrahydrofuran;water at 0 - 30; for 16 h;

Steps:

7 (2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (ii)
(2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (ii)
To a solution of (2S)-6-amino-2-(tert-butoxycarbonylamino)hexanoic acid (100.00 g, 406.01 mmol, 1.00 eq), NaHCO₃ (102.33 g, 1.22 mol, 3.00 eq) in THF (1000 mL) and H₂O (1000 mL) was added CbzOSu (101.19 g, 406.01 mmol, 1.00 eq) at 0° C.
Then the mixture was stirred at 30° C. for 16 hr.
The mixture was adjusted to pH=5-6 with 1N HCl, extracted with EA (600 mL*3), dried over Na₂SO₄, concentrated to give (2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (142.00 g, 373.26 mmol, 91.9% yield) as a yellow oil.

References:

Cortexyme, Inc.;KONRADI, Andrei;DOMINY, Stephen S.;CRAWFORD LYNCH, Casey;COBURN, Craig;VACCA, Joseph US2016/96830, 2016, A1 Location in patent:Paragraph 0368-0369

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24424-99-5 Synthesis