Methanol → Methyl 2-(4-hydroxy-1,2-oxazolidine-2-carbonyl)benzoate

温度

50 °C

Triethylamine (0.28 ml) was added to a solution of N-hydroxyphthalimide (5.00 g) and (R)-(+)-epichlorohydrin (2.40 ml) in anhydrous dioxane (10 ml) under nitrogen. The mixture was stirred at 50° C. for 48 h, further (R)-(+)-epichlorohydrin (0.24 ml) and triethylamine (0.28 ml) were added and stirring continued at 50° C. for 24 h. Methanol (10 ml) and further triethylamine (4.27 ml) were added and stirring continued at 50° C. for 2 h. The mixture was evaporated under reduced pressure, the residue dissolved in saturated aqueous sodium bicarbonate solution (100 ml) and extracted with ethyl acetate (6×100 ml). Combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was recrystallised from ethyl acetate to give the sub-title compound (3.4 g). MS(ESI) 252 [M+H]+. δ 1HCDCl3 3.66 (1H, d, br), 3.79 (1H, d, br), 3.89-3.99 (1H, m), 3.99-4.10 (1H, m), 4.74-4.81 (1H, m), 7.46 (1H, d), 7.49 (1H, t), 7.62 (1H, t), 7.99 (1H, d).

1. stirringstirring
2. waitcontinued at 50° C. for 24 h
3. stirringstirring
4. waitcontinued at 50° C. for 2 h
5. customThe mixture was evaporated under reduced pressure
6. dissolutionthe residue dissolved in saturated aqueous sodium bicarbonate solution (100 ml)
7. extractionextracted with ethyl acetate (6×100 ml)
8. dry with materialCombined organic extracts were dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customThe residue was recrystallised from ethyl acetate

ORDレコード

ord-bd9d612f13174c93bf7bc48d4777e4ce

出典データセット

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07384950B2