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ChemicalBook CAS DataBase List N-Boc-N'-Cbz-L-lysine
2389-45-9

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

13synthesis methods
-

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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