Pyridine → N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Temperature

25 °C

Anhydrous CrO3 (2.274 g, 22.74 mmol) is added to a solution of anhydrous pyridine (3.597 g, 45.48 mmol) in anhydrous CH2Cl2 (60 ml). After stirring at room temperature (25° C.) for 15 mins, the reaction mixture is treated all at once with a solution of N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one (1.432 g, 3.79 mmol) in anhydrous CH2Cl2 (25 ml). The resulting mixture is stirred at 25° C. for 5 mins. The CH2Cl2 layer is decanted from the dark, gummy residue which is triturated with more CH2Cl2. The combined CH2Cl2 phase is evaporated i.v. The residue is triturated with diethylether (Et2O) (100 ml) in several portions and the Et2O extracts are filtered to remove chromium salts. The etheral filtrate is washed with 5% NaHCO3, 1N HCl, 5% NaHCO3 and brine, dried with MgSO4, filtered, and evaporated i.v. to yield N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one (1.042 g) as a pale yellow oil:

1. stirringThe resulting mixture is stirred at 25° C. for 5 mins
2. customThe CH2Cl2 layer is decanted from the dark, gummy residue which
3. customis triturated with more CH2Cl2
4. customThe combined CH2Cl2 phase is evaporated i.v
5. customThe residue is triturated with diethylether (Et2O) (100 ml) in several portions
6. filtrationthe Et2O extracts are filtered
7. customto remove chromium salts
8. washThe etheral filtrate is washed with 5% NaHCO3, 1N HCl, 5% NaHCO3 and brine
9. dry with materialdried with MgSO4
10. filtrationfiltered
11. customevaporated i.v

ORD record

ord-c41d0c3e42724e06a850a82f01f84ffc

Source dataset

uspto-grants-1987_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04707547