ChemicalBook CAS DataBase List Boc-L-glutamic acid 1-tert-butyl ester

Boc-L-glutamic acid 1-tert-butyl ester synthesis

13synthesis methods

Product Name:Boc-L-glutamic acid 1-tert-butyl ester
CAS Number:24277-39-2
Molecular formula:C14H25NO6
Molecular Weight:303.35

24424-99-5 Synthesis

24424-99-5
841 suppliers
$13.50/25G

45120-30-7 Synthesis

45120-30-7
257 suppliers
$5.00/1g

24277-39-2
283 suppliers
$6.00/1g

Yield:24277-39-2 73%

Reaction Conditions:

with triethylamine in 1,4-dioxane;water at 25; for 16 h;

Steps:

3 The synthesis of intermediates I-86 and I-87:

To a mixture of (4S)-4-amino-5-tert-butoxy-5-oxo-pentanoic acid (50 g, 246 mmol) in dioxane (150 mL) and H₂O (150 mL) were added Et₃N (49.7 g, 492 mmol) and Boc₂O (59.1 g, 270 mmol). The mixture was stirred at 25°C for 16 h. The mixture was diluted with NaOH solution (2 M, 800 mL) and EtOAc (200 mL). The resulting solution was extracted with NaOH solution (2 M, 200 mL). HCl (aq., 6M) was added to the resulting aqueous layer above to adjust Ph~5. The resultant solution was extracted with EtOAc (500 mL × 2). The combined organic layers were washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated in vacuum to afford (S)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-5- oxopentanoic acid (I-80) (55 g, 73% yield) as an orange oil.¹H NMR (400 MHz, CDCl3) ^ 5.16 (d, J = 7.3 Hz, 1H), 4.29-4.15 (m, J = 5.0 Hz, 1H), 2.53-2.33 (m, 2H), 2.21-2.11 (m, 1H), 1.99-1.84 (m, 1H), 1.50-1.39 (m, 18H).

References:

WO2020/33784,2020,A1 Location in patent:Paragraph 00321