Isopropanol → [(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid

HRID 1719330Notes

Reaction equation

[CH3:1][C:2]([C@H:18]1[C@@H:21]([CH2:22][CH:23]=[O:24])[NH:20][C:19]1=[O:25])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6])[CH3:3].CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:3][C:2]([C@@H:18]1[C:19](=[O:25])[NH:20][C@@H:21]1[CH2:22][C:23]([OH:28])=[O:24])([O:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)=[O:6])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)azetidin-2-one (9 mg) in acetone (1 ml) was added 2N Jones reagent (60 μl) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. After addition of isopropyl alcohol (100 μl), the mixture was evaporated in vacuo. The residue was taken up in chloroform (20 ml) and washed with brine. The aqueous layer was extracted with chloroform (5 ml). The combined organic layers were washed with aqueous saturated sodium chloride, dried over magnesium sulfate, and evaporated to give {(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxo-azetidin-2-yl}acetic acid (7 mg).

Workup

customthe mixture was evaporated in vacuo
washwashed with brine
extractionThe aqueous layer was extracted with chloroform (5 ml)
washThe combined organic layers were washed with aqueous saturated sodium chloride
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-6c150de0314f4bb2bb0960fc45746bf0
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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