ChemicalBook CAS DataBase List S-3-N-Cbz-amino-2,6-Dioxo-piperidine

S-3-N-Cbz-amino-2,6-Dioxo-piperidine synthesis

4synthesis methods

Product Name:S-3-N-Cbz-amino-2,6-Dioxo-piperidine
CAS Number:22785-43-9
Molecular formula:C13H14N2O4
Molecular Weight:262.26

2650-64-8 Synthesis

2650-64-8
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$10.00/5g

22785-43-9
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$60.00/250mg

Yield:22785-43-9 90%

Reaction Conditions:

with 1,1'-carbonyldiimidazole in tetrahydrofuran; for 18 h;Reflux;Time;Temperature;Reagent/catalyst;

Steps:

6.2 6.2 Preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole- 1,3-dione (pomalidomide)

Into a stirring solution of carboxybenzyloxy-L-glutamine (2.8 g, 10 mmols) in 40 mL anhydrous THF, 1,1-carbonyldiimidazole (1.92 g, 12 mmols) were added. The reaction mixture was heated under reflux for 18 hours. The THF was evaporated and the product was dissolved in chloroform. The chloroform layer was washed with water and brine and dried over anhydrous CaSO₄, filtered and evaporated to give white solid. The solid product was crystallized from ethyl ether to give 2.4 grams crystalline powder (90%). (Alternatively, carboxybenzyloxy-L-glutamine can be cyclized by treating with SOCl₂ in Ν,Ν-dimethylformamide at -70°C to 0°C for 1 hour to form the product). The reaction mixture was diluted with CHCI₃ and washed with 5% Na₂CO₃, dried over anhydrous Na₂SO₄, filtered, and evaporated to give 2.5 g (90% yield) S(-)-(3- benzyloxycarbonylamino)-glutarimide). 1H NMR (CDCl₃) δ 8.2 (1H, s broad), 7.4 (5H, s, aromatic), 5.8 (1H, d), 5.15 (2H, s), 4.4 (1H, dd, J=4.5, 3), 2.95-2.4 (3H, m), 1.86 (1H, d, t, J=11.5, 6.5). m.p. 122-124°C (lit. 122-124°C)

References:

WO2014/39960,2014,A1 Location in patent:Page/Page column 57