cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone → trans-3-Acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone

HRID 231238Notes

Reaction equation

[Si:1]([N:8]1[C@H:11]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C@H:10]([C@H:18]([OH:20])[CH3:19])[C:9]1=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[C:18]([C@H:10]1[C@H:11]([C:12]#[C:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[N:8]([Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:9]1=[O:21])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

Cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.15 g) is dissolved in ethyl acetate (20 ml), and 5 g of activated manganese dioxide is added, followed by stirring at 25° C. for 5 hours. The manganese dioxide is filtered off and the filtrate is concentrated to give trans-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone (0.14 g).

Workup

filtrationThe manganese dioxide is filtered off
concentrationthe filtrate is concentrated

Sources & evidence

ORD record: ord-a70f07d30bb5450b8f1aafc39e97d89a
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845210

Reaction notes

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