2,6-Lutidine → HCID 53853337, compound

HRID 851373Notes

Reaction equation

O[CH:2]([N:7]1[C@H:10]([CH2:11][C:12](=[O:14])[CH3:13])[CH2:9][C:8]1=[O:15])[C:3]([O:5][CH3:6])=[O:4].N1C(C)=CC=CC=1C.S(Cl)([Cl:26])=O>O1CCCC1>[Cl:26][CH:2]([N:7]1[C@H:10]([CH2:11][C:12](=[O:14])[CH3:13])[CH2:9][C:8]1=[O:15])[C:3]([O:5][CH3:6])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 2-hydroxy-2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]acetate (268 mg) in tetrahydrofuran (5 ml) was cooled to -40° C. 2,6-Lutidine (0.287 ml) and thionyl chloride (0.18 ml) were added, and the mixture was stirred for one hour, during which time the temperature was allowed to warm to 0° C. The mixture was filtered and the filtrate was concentrated in vacuo to give methyl 2-chloro-2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]acetate. This product was diluted with benzene and concentrated in vacuo again. The residue was diluted with tetrahydrofuran (5 ml), and 2,6-lutidine (0.287 ml) and triphenylphosphine (650 mg) were added at 0° C. The mixture was stirred at room temperature for 15 hours, and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel (10 g) eluting with a mixture of ethyl acetate and acetone (10:1-10:5 ) to give methyl 2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]-2-(triphenylphosphoranylidene)acetate (350 mg) as an oil.

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4e55ea70cfa84c19a4597d27bc8a5b8e
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04383945

Reaction notes

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