L-Glutamic acid 5-tert-butyl ester synthesis
- Product Name:L-Glutamic acid 5-tert-butyl ester
- CAS Number:2419-56-9
- Molecular formula:C9H17NO4
- Molecular Weight:203.24
In a 3000mL three-necked flask, 2324g of tert-butyl acetate and 73.5g of glutamic acid were added, stirred, and was added dropwise. 160.8 mL of perchloric acid, react for 48 hours at 10°C, cool down to 0°C, add 1000 mL of water, extract (the remainin
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Yield:-
Reaction Conditions:
with piperidine in N,N-dimethyl-formamide for 0.5 h;
Steps:
Fmoc-Glu(O-t-Bu)-OH (compound 19, 67mg, 0.156 mmol) was treated with piperidine (20%) in DMF (1 mL) for 30 min. The solvent was removed in vacuo to afford the crude primary amine. A solution of 4-carboxy-Pennsylvania Green succinimidyl ester3 (25 mg, 0.052 mmol) in DMF (1 mL) was added to the crude primary amine in DMF (1 mL) followed by DIEA (0.25 mL). The reaction was allowed to stir at 22 0C for 16 h, dried in vacuo, and purified by flash column chromatography (MeOH, CH2C12, AcOH, 5:94.9:0.1) to afford compound 20 (27 mg, 90%) as an orange residue, mp 134- 138 0C; IH NMR (400 MHz, CD3OD) δ 8.00 (s, IH), 7.94 (dd, J = 7.9, 1.2 Hz, IH), 7.40 (d, J = 7.9 Hz, IH), 6.98 - 6.89 (m, 2H), 6.81 - 6.77 (m, 2H), 4.70 (dd, J = 9.6, 4.9 Hz, IH), 2.47 (t, J = 7.0 Hz, 2H), 2.39 - 2.27 (m, IH), 2.14 - 2.08 (m, IH), 2.12 (s, 3H), 1.46 (s, 9H); 13C NMR (101 MHz, CD3OD) δ 174.95, 173.97, 169.66, 156.19, 138.02, 137.15, 136.55, 131.01, 130.47, 126.62, 112.98, 112.76, 106.32, 81.94, 53.70, 32.95, 28.35 (t), 27.66, 19.60 ; IR (film) v max 2929, 1678, 1607, 1536, 1371, 1302, 1190, 1139, 953, 842, 801, 750, 724 cm-1; HRMS (ESI+) m/z 568.1779 (M+H+, C30H27F2NO8, requires 568.1705).
References:
UNIVERSITY OF KANSAS;THE PENN STATE RESEARCH FOUNDATION;PETERSON, Blake R. WO2011/19942, 2011, A2 Location in patent:Page/Page column 31-32
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