(R)-3-aminobutanoic acid → (R)-3-((tert-butoxycarbonyl)amino)butanoic acid

Temperature

0 °C

To a stirred suspension of (R)-3-aminobutanoic acid (2.415 g, 23.42 mmol) in dioxane (15 mL) and water (15.00 mL) was added TEA (4.90 mL, 35.1 mmol) dropwise. To the resulting light brown solution cooled at 0° C. was added portionwise di-tert-butyl carbonate (4.69 g, 26.9 mmol). The mixture was then stirred at rt for 16 hr. The reaction mixture was partitioned between water (80 mL) and EtOAc (80 mL). The separated aqueous layer was washed with EtOAc and acidified with 1 M aqueous KHSO4 to pH=3 and extracted with EtOAc (2×). The combined EtOAc extracts were washed with saturated aqueous NaCl (2×), dried over Na2SO4, filtered and concentrated to give (R)-3-(tert-butoxycarbonylamino)butanoic acid (4.301 g, 21.16 mmol, 90% yield) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.92 (s, 1H), 4.14-3.96 (m, 2H), 2.56 (d, J=5.2 Hz, 2H), 1.45 (s, 9H), 1.25 (d, J=6.9 Hz, 3H).

1. customThe reaction mixture was partitioned between water (80 mL) and EtOAc (80 mL)
2. washThe separated aqueous layer was washed with EtOAc
3. extractionextracted with EtOAc (2×)
4. washThe combined EtOAc extracts were washed with saturated aqueous NaCl (2×)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-26b6ee9900674cb79e140c975f066ac6

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346852B2