Benzyl acetate → N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl 2-hydroxypropyl)-azetidin-2-one

HRID 1154915Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[Si:20]([N:27]1[CH:30]([CH2:31][CH:32]=[O:33])[CH:29]([N:34]=[N+:35]=[N-:36])[C:28]1=[O:37])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>O1CCCC1>[Si:20]([N:27]1[CH:30]([CH2:31][CH:32]([OH:33])[CH2:2][C:1]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH:29]([N:34]=[N+:35]=[N-:36])[C:28]1=[O:37])([C:23]([CH3:25])([CH3:26])[CH3:24])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of benzyl acetate (0.011 mol) in anhydrous tetrahydrofuran (5 ml) is added dropwise to solution of lithium diisopropylamide (0.011 mol) in anhydrous tetrahydrofuran (20 ml) at -78° C. After stirring 15 more min at -78° C. the reaction mixture is treated dropwise with a solution of N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)-azetidin-2-one (0.01 mol) in tetrahydrofuran (10 ml). The mixture is stirred at -78° an additional 15 min and then quenched with 2.5 N hydrochloric acid (10 ml). The mixture is diluted with ethyl acetate, washed with water, 5% sodium bicarbonate solution, and brine, dried with magnesium sulfate, and evaporated under vacuum to afford N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl 2-hydroxypropyl)-azetidin-2-one.

Workup

stirringThe mixture is stirred at -78° an additional 15 min
customquenched with 2.5 N hydrochloric acid (10 ml)
additionThe mixture is diluted with ethyl acetate
washwashed with water, 5% sodium bicarbonate solution, and brine
dry with materialdried with magnesium sulfate
customevaporated under vacuum

Sources & evidence

ORD record: ord-9b44d0b96c4845fd9bec6323e0ba3501
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04298741

Reaction notes

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