Water → HCID 23387834, 화합물

HRID 989885

반응식

HRID 989885 반응식
[CH3:1][C:2]([CH3:13])([O:6][C:7]([O:9][CH:10](Cl)[CH3:11])=[O:8])[CH2:3][CH2:4][CH3:5].[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O-:36])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16].[Na+].O>CN(C=O)C.[Ag]I>[OH:14][C@@H:15]([C@H:17]1[C:37](=[O:38])[N:19]2[C:20]([C:34]([O:36][CH:10]([O:9][C:7]([O:6][C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4][CH3:5])=[O:8])[CH3:11])=[O:35])=[C:21]([C:24]3[S:28][C:27]4=[C:29]([S:32][CH3:33])[N:30]=[CH:31][N:26]4[CH:25]=3)[C@H:22]([CH3:23])[C@H:18]12)[CH3:16]

참가 물질

6

반응물 3

HCID 962WaterHCID 234491371-(1,1-Dimethyl-1-butyloxycarbonyloxy)ethyl chlorideHCID 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 23387834HCID 23387834, 화합물수율 29.9%

시약·촉매·용매 2

HCID 24563Silver iodide촉매HCID 6228Dimethylformamide용매3회

실험 절차

A solution of 156.6 mg of 1-(1,1-dimethyl-1-butyloxycarbonyloxy)ethyl chloride in 2.0 ml of DMF was added to a suspension of 176.1 mg of silver iodide in 2.0 ml of DMF. The mixture was stirred in an argon atmosphere at room temperature for one hr. A solution of 200.0 mg of sodium(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 in 1.0 ml of DMF was added thereto, followed by stirring for 3 hr. Water (10 ml) was added to the reaction solution to terminate the reaction. The system was extracted three times with 10 ml of ethyl acetate, followed by washing three times with 30 ml of semisaturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The residue was purified by chromatography on silica gel (chloroform:methanol=20:1) to give 82.3 mg of the title compound.

후처리

  1. stirringby stirring for 3 hr
  2. customto terminate
  3. customthe reaction
  4. extractionThe system was extracted three times with 10 ml of ethyl acetate
  5. washby washing three times with 30 ml of semisaturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe residue was purified by chromatography on silica gel (chloroform:methanol=20:1)

출처 및 근거

ORD 기록
ord-675901b43e19495ab0dd9350190c3749
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458780B1

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