Triethylamine → 3-Methanesulfonyloxy-1-[4-(p-nitrobenzyloxycarbonylaminomethyl)-1,3-thiazol-2-yl)azetidine

To a solution of 3-hydroxy-1-[4-(p-nitrobenzyloxycarbonylaminomethyl)-1,3-thiazol-2-yl]azetidine (457 mg, 1.25 mmol) (obtained as described in Reference Example 62(3)) in methylene chloride (25 ml) were added methanesulfonyl chloride (0.29 ml, 3.75 mmol) and triethylamine (0.53 ml, 3.80 mmol) in an ice bath. After stirring the mixture for 10 minutes in the ice bath, the resulting mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (1:1) as the eluant to afford 3-methanesulfonyloxy-1-[4-(p-nitrobenzyloxycarbonylaminomethyl)-1,3-thiazol-2-yl)azetidine (499.4 mg, yield 90%) as a yellow solid.

1. customthe completion of the reaction
2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
3. washThe organic layer was washed with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on a silica gel column

ORD-Eintrag

ord-7e1b11829d754507a77326e08b0dab2f

Quelldatensatz

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07001897B2