1-Methylimidazole → HCID 57550248, compound

HRID 548626Notes

Reaction equation

HRID 548626 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:6][C:5](=[O:7])[CH2:4]1.CN1C=CN=C1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(OCC)C>CN(C)C=O.O>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:1][CH2:2][C@@H:3]2[CH2:4][C:5](=[O:7])[NH:6]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 10964424(4S)-4-(hydroxymethyl)azetidin-2-one

Product 1

HCID 57550248HCID 57550248, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

(4S)-4-(hydroxymethyl)azetidin-2-one a39 (0.41 g, 4.6 mmol, 1 eq) and N-methylimidazole (1.1 ml, 14 mmol, 3.5 eq) are dissolved in dimethylformamide (5 ml) at 0° C. A solution of p-toluenesulfonyl chloride a40 (0.85 g, 4.4 mmol, 4 eq) in dimethylformamide (1 ml) is added dropwise. After 2 h, diethyl ether and water are added. The organic phase is separated, dried over magnesium sulfate and concentrated under reduced pressure to give 0.27 g of crude [(2S)-4-oxoazetidin-2-yl]methyl 4-methylbenzenesulfonate a41.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69e7aef9438e4ba5af81b53b84e62747
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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