L-Homoserine → Cbz-L-Homoserine

N-(Benzyloxycarbonyloxy)succinimide (23.57 g., 94.58 mmol.) was added to a solution of L-homoserine (10.24 g., 85.98 mmol.) and sodium bicarbonate (7.95 g., 94.58 mmol., 1.1 eq.) in a mixture of water (100 ml.) and acetone (100 ml.). The mixture was stirred at room temperature overnight. The acetone was removed under reduced pressure (rotovap) and the aqueous solution was washed with methylene chloride (2×75 ml.). The aqueous layer was then acidified to pH 2 by addition of 6N hydrochloric acid and extracted with ethyl acetate (2×250 ml.). The combined ethyl acetate layers were washed with water (2×100 ml.) and brine, dried over sodium sulfate, filtered, concentrated and dried in vacuo to afford 19.54 g. of title product as a white solid. TLC (ethyl acetate:n-butanol:acetic acid:water; 2:1:1:1) Rf =0.74

1. customThe acetone was removed under reduced pressure (rotovap)
2. washthe aqueous solution was washed with methylene chloride (2×75 ml.)
3. additionThe aqueous layer was then acidified to pH 2 by addition of 6N hydrochloric acid
4. extractionextracted with ethyl acetate (2×250 ml.)
5. washThe combined ethyl acetate layers were washed with water (2×100 ml.) and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customdried in vacuo
10. customto afford 19.54 g

ORD record

ord-c8e0c1a9541c4f15b6c08cafff1fb08a

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05508272