Tert-Butyl nitrite → (S)-2-Acetoxybutanoic acid

Temperature

60 °C

Sodium acetate (11.9 g, 146 mmol) and tert-butyl nitrite (15.0 g, 146 mmol) were added to an acetic acid (300 mL) solution of (2S)-2-aminobutyric acid (10.0 g, 97.0 mmol) under ice cooling, and was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was washed with water and brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Furthermore, the residue was azeotropically boiled with 1,4-dioxane (50 mL) twice. Thus, the title compound (8.4 g, yield: 60%) was obtained.

1. temperatureThe reaction mixture was cooled to room temperature
2. distillationthe solvent was distilled off under reduced pressure
3. additionWater was added to the residue
4. extractionthe mixture was subjected to extraction twice with ethyl acetate
5. customThe organic layer thus obtained
6. washwas washed with water and brine
7. dry with materialwas dried over anhydrous sodium sulfate
8. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-b6b169fe7a934fdfb1416952db2aa9cf

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006273B2