Sodium Chloride → HCID 70214140, compound

HRID 565241Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[Sn](CCCC)(CCCC)CCCC)[C:9]1=[O:29].[Cl:30][C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1.[OH-].[NH4+].[Cl-].[Na+]>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[C:34]2[CH:35]=[CH:36][C:31]([Cl:30])=[CH:32][CH:33]=2)[C:9]1=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-tributylstannyl-2-propene-1-yl)-4-methylazetidin-2-one (0.92 g, 1.79 mmol) in 3 mL of dimethylformamide is added 4-chloroiodobenzene (470 mg, 1.97 mmol) and triphenyphosphine palladium (II) dichloride (63 mg, 0.09 mmol). The resulting solution is heated at 80° C. for 16 h, then 0.5 mL ammonium hydroxide is added. The reaction mixture is poured into saturated sodium chloride solution (20 mL) and extracted with 1:1 ethyl acetate/hexane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (elution with 3:1 hexanes-ethyl acetate) to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-(4-chlorophenyl)-2-propene-1-yl)-4-methylazetidin-2-one as an oil (370 mg, 61% yield).

Workup

extractionextracted with 1:1 ethyl acetate/hexane (50 mL)
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified by silica gel chromatography (elution with 3:1 hexanes-ethyl acetate)

Sources & evidence

ORD record: ord-6da4f911366e486997d1c4dae6a10731
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172064B2

Reaction notes

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