L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT synthesis

7synthesis methods

Product Name:L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT
CAS Number:16874-06-9
Molecular formula:C13H25NO4
Molecular Weight:259.34

56-86-0 Synthesis

56-86-0
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L-GLUTAMIC ACID DI-TERT-BUTYLESTER DIBEN ZENESULFIMIDE SALT

16874-06-9
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Yield: 94%

Reaction Conditions:

with sulfuric acid in dichloromethane at -78 - 21; for 120 h;

Steps:

15 PREPARATION EXAMPLE 15 Di-tert-butyl L-glutamate (24)
A suspension of L-glutamic acid (1.47 g, 10.0 mmol) in dry CH₂CI₂ (40 mL) was placed in a pressure bottle and treated with concentrated H₂S0₄ (1.5 mL). The mixture was cooled to -78 oC followed by addition of condensed isobutylene (25 mL) within the pressure bottle at the same temperature. The bottle was closed and the reaction mixture was stirred at 21 oC for 5 days. Then the pressure bottle was cool to -78 oC and opened to dilute the reaction mixture with EtOAc (100 mL) followed by addition of sat. aq. NaHC0₃ (100 mL). The organic phase was separated and the aqueous phase washed with EtOAc (3 x 25 mL). The organic phases were collected, dried over Na₂S0₄, filtered, and concentrated in vacuo to afford a clear oil. Purification by flash column chromatography on silica gel using a mixture of EtOAc/Hep (4/1, v/v) as the eluent afforded the title compound 24 as a clear oil ( 1.26 g, 94%) . Rf = 0.35 (silica, eluent EtOAc) . ^XH NMR (400 MHz, C₅D₅) δ 3.17 (dd, J = 8.6, 4.9 Hz, 1H), 2.40 - 2.34 (m, 2H), 2.10 - 1.99 (m, 1H), 1.82 - 1.70 (m, 1H), 1.37 (s, 9H), 1.31 (s, 9H), 0.98 (br s, 1H), 0.44 (br s, 1H) ; 13C NMR (101 MHz, C₅D₅) δ 175.1, 172.4, 80.2, 79.6, 54.7, 32.1, 30.6, 28.1, 28.0.

References:

DANMARKS TEKNISKE UNIVERSITET;PEIRÓ CADAHÍA, Jorge;CLAUSEN, Mads, Hartvig;BONDEBJERG, Jon;HANSEN, Christian, Abildgaard WO2018/37120, 2018, A1 Location in patent:Page/Page column 44; 45; 49