Dimethylformamide → HCID 131718111, 화합물

HRID 5063노트

반응식

HRID 5063 반응식
[CH3:1][C:2]1[O:6][C:5](=[O:7])[O:4][C:3]=1[CH2:8]I.[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O-:24])=[O:23])[CH2:14][CH2:13][NH:12]1.[Na+].CN(C)C=O>C(Cl)(Cl)Cl.C(OCC)(=O)C>[O:10]=[C:11]1[CH:15]([S:16][C:17]2[C@H:18]([CH3:31])[C@@H:19]3[C@@H:26]([C@H:27]([OH:29])[CH3:28])[C:25](=[O:30])[N:20]3[C:21]=2[C:22]([O:24][CH2:8][C:3]2[O:4][C:5](=[O:7])[O:6][C:2]=2[CH3:1])=[O:23])[CH2:14][CH2:13][NH:12]1

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 189421374-(Iodomethyl)-5-methyl-2H-1,3-dioxol-2-oneHCID 131718112HCID 131718112, 화합물

생성물 1

HCID 131718111HCID 131718111, 화합물수율 45.7%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 0.4 ml of dry dimethylformamide. The mixture was stirred at room temperature for 80 minutes and then at 30°-45° C. for 4.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed four times with an aqueous solution of sodium chloride. The extract was dried and the solvent was distilled off under reduced pressure. The residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A), eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 27.4 mg of the title compound in the form of a colorless powder.

후처리

  1. waitat 30°-45° C. for 4.5 hours
  2. washwashed four times with an aqueous solution of sodium chloride
  3. customThe extract was dried
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A),
  6. washeluted with a 10:1 by volume mixture of ethyl acetate and methanol

출처 및 근거

ORD 기록
ord-d17197b3300b4c588249b50f58b34560
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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