tert-Butyl acetate → L-Glutamic acid di-tert-butyl ester

Acetic acid 1,1-dimethylethyl ester (1742 g; 2 L; 15 mol) (commercial product), 70% aq. perchloric acid (51 mL; 0.59 mol) and L-glutamic acid (78.8 g; 0.54 mol) (commercial product) were stirred at 25° C. over 5 days. After addition of a solution of K2CO3 (41.46 g, 0.3 mol) in H2O (140 mL) to the reaction mixture, the organic phase was separated, washed with water (2×500 mL), dried (NaSO4) and concentrated to dryness. The residue (27.2 g) was dissolved in Et2O (200 mL) and extracted with 1N HCl (2×70 mL), the combined aqueous phase was washed with Et2O (40 mL) and collected with the aqueous phases previously obtained from the first neutralization and successive washings. Addition of 10 N NaOH up to pH 8.8 led to an emulsion which was extracted with Et2O (2×600 mL). The combined organic phases were washed with H2O (250 mL), dried and evaporated to give the desired compound (57.7 g; 0.22 mol). Yield 41%.

1. customthe organic phase was separated
2. washwashed with water (2×500 mL)
3. dry with materialdried (NaSO4)
4. concentrationconcentrated to dryness
5. dissolutionThe residue (27.2 g) was dissolved in Et2O (200 mL)
6. extractionextracted with 1N HCl (2×70 mL)
7. washthe combined aqueous phase was washed with Et2O (40 mL)
8. customcollected with the aqueous phases
9. custompreviously obtained from the first neutralization and successive washings
10. extractionwas extracted with Et2O (2×600 mL)
11. washThe combined organic phases were washed with H2O (250 mL)
12. customdried
13. customevaporated

ORD 기록

ord-7255903b82b040459b8d14d1553a6454

출처 데이터셋

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06403055B1