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Phosphate → (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic Acid

HRID 382617
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HRID 382617 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[S:14][C:13]4=[CH:15][N:16]=[CH:17][N:12]4[CH:11]=3)[CH2:9][C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:31](=[O:32])[N:6]2[C:7]([C:18]([OH:20])=[O:19])=[C:8]([C:10]3[S:14][C:13]4=[CH:15][N:16]=[CH:17][N:12]4[CH:11]=3)[CH2:9][C@H:5]12)[CH3:3]
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참가 물질

5

반응물 2

HCID 1061PhosphateHCID 120700434-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 12069978(5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic Acid수율 19.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of 41 mg of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate in 2 ml of THF and 2 ml of {fraction (1/15)} M phosphate buffer (pH 6.8) was added 61 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 2 hours. The catalyst was removed by filtration on Celite and washed with water. The filtrate was washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 to give 5.7 mg of the title compound.

후처리

  1. customThe reactor was purged with hydrogen
  2. customThe catalyst was removed by filtration on Celite
  3. washwashed with water
  4. washThe filtrate was washed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20

출처 및 근거

ORD 기록
ord-ed46f07436f34b369fcb9567da5e1fe9
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06310056B1

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