Methanol → HCID 86588485, compound

Temperature

0 °C

To a solution of N-(t-butoxycarbonyl)-2(S)-benzyloxycarbonylamino-β-alanine (6.15 g) in methanol (120 ml) was added 10% Pd—C (50% wet, 1.2 g). The mixture was stirred vigorously, and hydrogen gas was bubbled for 1 hour. The catalyst was removed by filtration, and the filtrate was evaporated in vacuo. The residue was dissolved in tetrahydrofuran (70 ml) and cooled to 0° C. with ice bath. 1N NaOH (36 ml) was added, then acetic anhydride (3.77 ml) was added dropwise under stirring. The mixture was stirred for additional 1 hour at 0° C., then the pH of the mixture was adjusted to 2.5 with aqueous 20% KHSO4. The resultant mixture was extracted with ethyl acetate-tetrahydrofuran (200 ml-100 ml) twice times. The combined organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was recrystallized from diethyl ether to give N-(t-butoxycarbonyl)-2(S)-acetylamino-β-alanine (3.17 g).

1. customhydrogen gas was bubbled for 1 hour
2. customThe catalyst was removed by filtration
3. customthe filtrate was evaporated in vacuo
4. dissolutionThe residue was dissolved in tetrahydrofuran (70 ml)
5. addition1N NaOH (36 ml) was added
6. additionacetic anhydride (3.77 ml) was added dropwise
7. stirringunder stirring
8. stirringThe mixture was stirred for additional 1 hour at 0° C.
9. extractionThe resultant mixture was extracted with ethyl acetate-tetrahydrofuran (200 ml-100 ml) twice times
10. dry with materialThe combined organic layer was dried over Na2SO4
11. customevaporated in vacuo
12. customThe residue was recrystallized from diethyl ether

ORD record

ord-4a4f25646b6f45e0a579f48e2c0acbbc

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06538007B1