Boc-L-glutamic acid 1-tert-butyl ester synthesis
- 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
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45120-30-7
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24277-39-2
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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
24277-38-1
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24277-39-2
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28812-54-6
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24277-39-2
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91229-91-3
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24277-39-2
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56-86-0
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24277-39-2
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