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ChemicalBook CAS DataBase List Boc-beta-alanine

Boc-beta-alanine synthesis

8synthesis methods
-

Yield:3303-84-2 90%

Reaction Conditions:

with water;lithium hydroxide in ethanol at 20; for 5 h;

Steps:

Intermediate I-i 3B: 3 -((tert-butoxycarbonyl)amino)propanoic acid
Ethyl 3-((tert-butoxycarbonyl)amino)propanoate (1.4, 6.44 mmol) was dissolved in ethanol (10 mL) and a solution of lithium hydroxide (0.154 g, 6.44 mmol) in water (10 mL) was added. The reaction mixture was stirred at room temperature for 5 hrs. The reaction mixture was concentrated in vacuo to provide a cmde residue which wasdissolved in water and washed with DCM. The aqueous layer was neutralized with 6NHC1 and the solid obtained was filtered and dried under vacuum to afford 3-((tert-butoxycarbonyl)amino)propanoic acid (1.1 g, 90 %yield) as a white solid. LCMS m/z188.2 (M-H); ‘HNMR(400 MHz, MeOD) ö 3.29 (t,J= 11.20Hz, 2H), 2.47 (t,J= 13.60Hz, 2H), 1.43 (s, 9H).

References:

BRISTOL-MYERS SQUIBB COMPANY;DUNCIA, John V.;GARDNER, Daniel S.;HYNES, John;MACOR, John E.;MURUGESAN, Natessan;SANTELLA, Joseph B.;WU, Hong;KANTHETI, Durgarao;NAIR, Satheesh Kesavan;PAIDI, Venkatram Reddy;RATNA KUMAR, Sreekantha;SARKUNAM, Kandhasamy;SISTLA, Ramesh Kumar;POLIMERA, Subba Rao WO2016/210036, 2016, A1 Location in patent:Page/Page column 121

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