Ethyl Acetate → HCID 23387866, 화합물

HRID 1839347

반응식

HRID 1839347 반응식
[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O-:23])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[CH3:27][O:28][C:29]1[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=1[C:31]([O:33][CH2:34]Cl)=[O:32].[C:40](OCC)(=O)C>CN(C=O)C.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[OH:1][C@@H:2]([C@H:4]1[C:24](=[O:25])[N:6]2[C:7]([C:21]([O:23][CH:34]([O:33][C:31](=[O:32])[C:30]3[CH:36]=[CH:37][CH:38]=[CH:39][C:29]=3[O:28][CH3:27])[CH3:40])=[O:22])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH3:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 23449271HCID 23449271, 화합물HCID 23669370Sodium (1s,5r,6s)-6-((1r)-1-hydroxyethyl)-1-methyl-2-(7-methylthio-imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 23387866HCID 23387866, 화합물

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6228Dimethylformamide용매

실험 절차

Sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-methylthioimidazo[5,1-b]thiazol2-yl)-1-carbapen-2-em-3-carboxylate (170 mg) was dissolved in 2 ml of DMF. Triethylbenzylammonium chloride (193 mg) and 182 mg of 2-methoxybenzoyloxymethyl chloride were added to the solution in an argon atmosphere. The mixture was stirred under ice cooling for 2 hr and then stirred at room temperature for 5 hr. Ethyl acetate (30 ml) was added to the reaction solution. The mixture was washed twice with 20 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated to a volume of 5 ml under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1) to give 131 mg of the title compound.

후처리

  1. stirringstirred at room temperature for 5 hr
  2. washThe mixture was washed twice with 20 ml of semisaturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a volume of 5 ml under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane: methanol=40: 1)

출처 및 근거

ORD 기록
ord-969dd61671a94d4e94269ab287b6d977
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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