Potassium Bicarbonate → (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one

Temperature

0 °C

To a solution of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(1,2,4-trioxolan-3-yl)-methylazetidin-1-yl]-2-oxoacetate (205 mg) in methanol (4 ml) was added 1N aqueous potassium hydrogen carbonate (0.5 ml) at ambient temperature. The mixture was stirred for 25 minutes and cooled to 0° C. Sodium borohydride (40 mg) and 1N aqueous potassium hydrogen carbonate were added to the mixture at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for an additional 30 minutes, and quenched by addition of acetic acid (0.20 ml). The resulting mixture was concentrated under reduced pressure and the residue was dissolved in chloroform and washed with brine containing sodium hydrogen carbonate. The aqueous layer was extracted three times with chloroform. The combined extracts were dried over magnesium sulfate, evaporated in vacuo, and chromatographed on silica gel (3 g, eluting with 10-30% acetone in dichloromethane) to give 66 mg of (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one.

1. stirringThe reaction mixture was stirred at 0° C. for 30 minutes and at ambient temperature for an additional 30 minutes
2. customquenched by addition of acetic acid (0.20 ml)
3. concentrationThe resulting mixture was concentrated under reduced pressure
4. dissolutionthe residue was dissolved in chloroform
5. washwashed with brine
6. additioncontaining sodium hydrogen carbonate
7. extractionThe aqueous layer was extracted three times with chloroform
8. dry with materialThe combined extracts were dried over magnesium sulfate
9. customevaporated in vacuo
10. customchromatographed on silica gel (3 g, eluting with 10-30% acetone in dichloromethane)

ORD record

ord-b6bc4366db504ba0a77907de18156a23

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04539152