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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
ノート
印刷プレビュー

反応式

HRID 382617 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed46f07436f34b369fcb9567da5e1fe9
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06310056B1

反応ノート

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