Dimethyl Sulfoxide → (3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

HRID 64802Notes

Reaction equation

FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[Si:18]([N:25]1[C@H:28]([CH2:29][C:30]([S:35][CH3:36])([S:33][CH3:34])[S:31][CH3:32])[CH:27]([CH:37]([OH:39])[CH3:38])[C:26]1=[O:40])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Si:18]([N:25]1[C@H:28]([CH2:29][C:30]([S:35][CH3:36])([S:33][CH3:34])[S:31][CH3:32])[C@@H:27]([C:37](=[O:39])[CH3:38])[C:26]1=[O:40])([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: -78 °C

Procedure

Trifluoroacetic anhydride (400 mg., 1.905 mmol) is added by syringe to a solution of dimethyl sulfoxide (2.53 mmol) in dry methylene chloride (5 ml) at -78° C. The resulting mixture is stirred at -78° C. for 30 minutes prior to the addition of a solution of (3RS,4R)-1-(t-butyldimethylsilyl)-3-[(RS)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one (500 mg., 1.27 mmol) in dry CH2 cl2 (1 ml). The resulting solution is stirred for 30 minutes prior to the addition of triethylamine (360 mg., 3.56 mmol). The cooling bath is removed. After 40 minutes, the reaction mixture is diluted with CH2Cl2, washed with water and brine and dried over magnesium sulfate. Removal of solvents in vacuo gives an oil which is purified as above. Yields 432 mg. (86%).

Workup

stirringThe resulting solution is stirred for 30 minutes
customThe cooling bath is removed
waitAfter 40 minutes
additionthe reaction mixture is diluted with CH2Cl2
washwashed with water and brine
dry with materialdried over magnesium sulfate
customRemoval of solvents in vacuo
customgives an oil which
customis purified as above
customYields 432 mg

Sources & evidence

ORD record: ord-b823a896e9dc47d1ac5e80ccb653f712
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04610820

Reaction notes

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