trans-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone → trans-4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone

HRID 231231Notes

Reaction equation

HRID 231231 reaction equation
[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[CH:10]([O:12][Si](C(C)(C)C)(C)C)[CH3:11])(=[O:3])[CH3:2]>C(O)(=O)C.O>[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[CH:10]([OH:12])[CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 67757824trans-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone

Product 1

HCID 67789253trans-4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinoneYield 24.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Trans-4-acetoxy-3-[1-(tert-butyldimethylsilyloxy)-ethyl]-2-azetidinone (0.20 g) is dissolved in a mixture of acetic acid (5 ml) and water (2 ml), and the solution is stirred at 70°-80° C. for 2.5 hours and then concentrated under reduced pressure. The residue is subjected to silica gel column chromatography to give 0.03 g of trans-4-acetoxy-3-(1-hydroxyethyl)-2-azetidinone.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0ad439e23884e80974957d04dd3358d
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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