(R)-3-Isopropyl-2,5-piperazinedione synthesis

8synthesis methods

Product Name:(R)-3-Isopropyl-2,5-piperazinedione
CAS Number:143673-66-9
Molecular formula:C7H12N2O2
Molecular Weight:156.18

Glycine, N-[(phenylmethoxy)carbonyl]-D-valyl-, methyl ester

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143673-66-9
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Yield: 53%

Reaction Conditions:

Stage #1:N-benzyloxycarbonyl-(2R)-valinylglycine methyl ester with 5%-palladium/activated carbon;hydrogen in tetrahydrofuran at 20; under 775.743 Torr; for 2 h;
Stage #2: in toluene at 110 - 130; for 20 h;

Steps:

58
[0560] To a solution of compound 4-01-3 (40.0 g, 120 mmol) in tetrahydrofuran (100 mL) was added 5% palladium on carbon (1 g). The mixture was degassed, purged with hydrogen, and stirred at 20°C for 2 hours under hydrogen (15 psi) atmosphere. The solution was filtered through celite and concentrated under reduced pressure. The residue was dissolved in toluene (300 mL) and then stirred at 130°C for 8 hours, then stirred at 1 10°C for 12 hours. The suspension mixture was cooled to 0°C. The solid was filtered and washed with petroleum ether (500 mL *2) to afford compound 4-01-4 (11 g, 53% yield) as a white solid.

References:

CORNELL UNIVERSITY;TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE;LIN, Gang;NATHAN, Carl;KIRKMAN, Laura;ZHAN, Wenhu;MORGAN, Trevor;SATO, Kenjiro;HARA, Ryoma;KAWASAKI, Masanori;IMAEDA, Toshihiro;TOITA, Akinori;OKAMOTO, Rei;YUKAWA, Takafumi;ASO, Kazuyoshi;WONG, Tzu-Tshin;GINN, John, D.;FOLEY, Michael, A. WO2019/75259, 2019, A1 Location in patent:Paragraph 0560