ChemicalBook CAS DataBase List TERT-BUTYL-(2S,4R)-N'-(BENZYLOXYCARBONYL)-N'-(BENZYLOXYCARBONYL)-4-HYDROXYORNITHINATE

TERT-BUTYL-(2S,4R)-N'-(BENZYLOXYCARBONYL)-N'-(BENZYLOXYCARBONYL)-4-HYDROXYORNITHINATE synthesis

8synthesis methods

Product Name:TERT-BUTYL-(2S,4R)-N'-(BENZYLOXYCARBONYL)-N'-(BENZYLOXYCARBONYL)-4-HYDROXYORNITHINATE
CAS Number:371972-14-4
Molecular formula:C22H34N2O7
Molecular Weight:438.51

31139-36-3
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L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-4-hydroxy-, 1,1-dimethylethyl ester, (4R)-

371972-12-2
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TERT-BUTYL-(2S,4R)-N'-(BENZYLOXYCARBONYL)-N'-(BENZYLOXYCARBONYL)-4-HYDROXYORNITHINATE

371972-14-4
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Yield:371972-14-4 83%

Reaction Conditions:

in tetrahydrofuran;dichloromethane at 0; for 1 h;

Steps:

Synthesis of tert-butyl (^-^-[(benzyloxyJcarbonylJ-A^-^ert-butoxycarbonyl)^- hydroxy-L-ornithinate (26):; To a solution of dibenzyldicarbonate (600 mg, 2.09 mmol) in tetrahydrofurane (12.5 mL) was added at 0⁰C a solution of (4) (455 mg, 1.50 mmol) in tetrahydrofurane/dichloromethane (1:1 , 5 mL). After stirring for 1 h at this temperature the reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (20 mL). The layers were separated, the aqueous phase extracted with ethyl acetate (3 x 20 mL), the combined organic layers dried over sodium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography (silica, hexane/ethyl acetate). Yield: 548 mg, 83 %.¹H-NMR (300MHz, CHLOROFORM-d): δ [ppm]= 1.45 (s, 9H), 1.47 (s, 9H), 1.68 - 1.84 (m, 1 H), 1.90 - 2.02 (m, 1 H), 3.13 (ddd, 1 H), 3.28 - 3.51 (m, 2H), 3.91 (br. s., 1H), 4.22 (dd, 1 H), 5.11 (s, 2H), 5.23 (br. s., 1 H), 5.39 (br. s., 1 H), 7.29 - 7.40 (m, 5H). MS (ESIpos): m/z = 439 [M+H]⁺

References:

WO2010/63403,2010,A2 Location in patent:Page/Page column 56

34582-32-6 Synthesis