Oxalic Acid → HCID 57110945, compound

HRID 1464724

Reaction equation

FC(F)(F)S([O-])(=O)=O.[Sn+2].FC(F)(F)S([O-])(=O)=O.[C:18]([S:22][CH3:23])(=[S:21])[CH2:19][CH3:20].C(O[C@H:28]1[NH:31][C:30](=[O:32])[C@@H:29]1[C@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH3:34])(=O)C.C(O)(=O)C(O)=O>ClCCl.C(N(CC)CC)C>[C:39]([Si:36]([CH3:37])([CH3:38])[O:35][C@@H:33]([C@@H:29]1[C@@H:28]([S:21][C:18]([S:22][CH3:23])=[CH:19][CH3:20])[NH:31][C:30]1=[O:32])[CH3:34])([CH3:40])([CH3:41])[CH3:42]

Participants

Conditions

Temperature: -25 °C

Procedure

To a suspension of Tin(II) trifluoromethanesulfonate (5.58 g) in dichloromethane (27 ml) cooled to -25° C. were added triethylamine (1.62 g) and methyl dithiopropionate (1.20 g) successively. The mixture was stirred for 2 hours at -20° C. and (3R,4R)-4-acetoxy-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidine (2.0 g) was added thereto. After stirring for 2 hours at 0° C., the mixture was poured into 20% aqueous solution of oxalic acid (100 ml) and the precipitates were filtered off. The organic layer of the filtrate was separated, dried, and concentrated under reduced pressure. The residue was purified by silica gel (50 g) column chromatography (20% ethyl acetate-hexane) to afford (3S,4R)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1-methylthio-1-propenyl)thio]-2-oxoazetidine (mixture of E and Z isomers) (1.14 g).

Workup

stirringAfter stirring for 2 hours at 0° C.
filtrationthe precipitates were filtered off
customThe organic layer of the filtrate was separated
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel (50 g) column chromatography (20% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-18770e975bdd4ca0bab87590ee064ff8
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306816

Linked notes

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