Oxalic Acid → HCID 57110945, 화합물

HRID 1464724

반응식

HRID 1464724 반응식
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]

참가 물질

7

반응물 4

HCID 971Oxalic AcidHCID 223580Methyl propanedithioateHCID 2776843Tin(II) trifluoromethanesulfonateHCID 10935078Azetidon

생성물 1

HCID 57110945HCID 57110945, 화합물수율 47.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
-25 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-18770e975bdd4ca0bab87590ee064ff8
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306816

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