(S)-methyl 2-(bis(tert-butoxycarbonyl)amino)-4-oxobutanoate synthesis
- Product Name:(S)-methyl 2-(bis(tert-butoxycarbonyl)amino)-4-oxobutanoate
- CAS Number:219617-09-1
- Molecular formula:C15H25NO7
- Molecular Weight:331.36
219617-08-0
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219617-09-1
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Yield:219617-09-1 99%
Reaction Conditions:
with diisobutylaluminium hydride in diethyl ether;cyclohexane at -78 - 20; for 1.5 h;Inert atmosphere;
Steps:
Methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]-carbonylamino}-4-oxo-butanoate (S3a)
The diester S2a (3.61 g, 10.0 mmol) was dissolved in abs. Et2O (80 mL) under N2-atmosphere. At -78 °C, a solution of DIBAL-H (10.0 mL, 11.0 mmol, 1.1 M in cyclohexane) was added slowly and the reaction mixture was stirred at -78 °C for 1.5 h. After warming to room temperature, demin. water (1.26 mL) was added to stop the reaction. The reaction mixture was filtered through a pad of Celite and eluated with Et2O (2 x 40 mL). After evaporation of the solvent, the residue was purified by column chromatography on silica gel (hexanes/EtOAc 2 : 1) to give aldehyde S3a as a colourless oil (3.34 g, 10.0 mmol, >99 %).Rf = 0.66 (hexanes/EtOAc 2 : 1, KMnO4). 1H-NMR (500 MHz, CDCl3): δ = 1.51 (s, 18H, 2 x C(CH3)3),2.83 (dd, J = 17.9, 6.0 Hz, 1H, 3-Ha), 3.42 (dd, J = 17.9, 6.8 Hz, 1H, 3-Hb), 3.74 (s, 3H, CO2CH3), 5.53 (dd, J = 6.8, 6.0 Hz, 1H, 2-H), 9.80 (s, 1H, 4-H) ppm. 13C-NMR (125 MHz, CDCl3): δ = 28.0 (2 x C(CH3)3), 45.0 (C-3), 52.6 (CO2CH3), 52.9 (C-2), 83.7 (2 x C(CH3)3), 151.7 (2 x C=OBoc), 170.3 (C-1), 198.4 (C-4) ppm. The spectroscopic data are in accordance with the literature.[1]
References:
Sch?del, Nicole;Icik, Esra;Martini, Maike;Altevogt, Luca;Ramming, Isabell;Greulich, Andreas;Baro, Angelika;Bilitewski, Ursula;Laschat, Sabine [Synthesis,2021,vol. 53,# 13,p. 2260 - 2268] Location in patent:supporting information
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