Methyl iodide → (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-methoxycarbonylmethyl-2-oxoazetidine

HRID 1650302Notes

Reaction equation

[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([OH:18])=[O:17])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O.O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([O:18][CH3:20])=[O:17])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidine (302.6 mg) in dimethylformamide (10 ml) was added potassium carbonate (160 mg) at ° C. After 10 minutes, to the mixture was added dropwise methyl iodide (68.8 μ1). After stirring at 0° C. for 1.5 hours, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (30 ml). The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave (3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-methoxycarbonylmethyl-2-oxoazetidine (285.5 mg).

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customEvaporation of the solvent

Sources & evidence

ORD record: ord-eee41e1f7ceb4530bd5028520298fbc1
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923857

Reaction notes

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