Phosphate → (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(6-methylimidazo[5,1-b]thiazolium-3-yl)-1-carbapen-2-em-3-carboxylate

HRID 382626노트

반응식

HRID 382626 반응식
[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])=[C:8]([C:10]3[N:11]4[CH:17]=[N:16][CH:15]=[C:12]4[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3].I[CH3:34].P([O-])([O-])([O-])=O>ClCCl.C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([O-:20])=[O:19])=[C:8]([C:10]3[N+:11]4[C:12](=[CH:15][N:16]([CH3:34])[CH:17]=4)[S:13][CH:14]=3)[CH2:9][C@H:5]12)[CH3:3]

참가 물질

7

반응물 3

HCID 1061PhosphateHCID 6328Methyl iodideHCID 1317229034-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 178462294(5R,6S)-6-((1R)-1-hydroxyethyl)-2-(6-methylimidazo[5,1-b]thiazolium-3-yl)-1-carbapen-2-em-3-carboxylate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 100 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-carbapen-2-em-3-carboxylate in 1.5 ml of dry dichloromethane was added 1.37 ml of iodomethane, and the mixture was stirred under the atmosphere of argon in the darkness at room temperature for 24 hours. Unreacted reagent was removed under reduced pressure. The residue thus obtained was dissolved in 4 ml of THF and 4 ml of 1/15 M phosphate buffer (pH 6.8), and 160 mg of 10% Pd-C was added. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 3.5 hours. The catalyst was collected by filtration on Celite and washed with water. The filtrate was washed with ethyl acetate, and purified by column chromatography on DIAION HP-20 and COSMOSEAL 40C18-PREP (water:methanol=20:1) to give 4.8 mg of the title compound.

후처리

  1. customwas removed under reduced pressure
  2. customThe residue thus obtained
  3. customThe reactor was purged with hydrogen
  4. stirringthe reaction mixture was stirred at room temperature for 3.5 hours
  5. filtrationThe catalyst was collected by filtration on Celite
  6. washwashed with water
  7. washThe filtrate was washed with ethyl acetate
  8. custompurified by column chromatography on DIAION HP-20 and COSMOSEAL 40C18-PREP (water:methanol=20:1)

출처 및 근거

ORD 기록
ord-ed90a141c07745dc8eb3b34c7222537b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310056B1

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