Oxalic Acid → HCID 57110945、化合物

HRID 1464724

反応式

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]

参加物

反応条件

温度: -25 °C

実験手順

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).

後処理

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)

出典と根拠

ORDレコード: ord-18770e975bdd4ca0bab87590ee064ff8
出典データセット: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US05306816

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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