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

HRID 382619ノート

反応式

HRID 382619 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([O:22]CC3C=CC([N+]([O-])=O)=CC=3)=[O:21])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[C:12]=3[CH3:19])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O.C(NCC1N=CN2C(C3C[C@@H]4[C@@H]([C@H](O)C)C(=O)N4C=3C([O-])=O)=CSC=12)=O.[Na+]>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:20]([OH:22])=[O:21])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[C:12]=3[CH3:19])[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

6

反応物 3

HCID 1061PhosphateHCID 120700444-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(3-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylateHCID 131722902Sodium (5R,6S)-2-(7-formylaminomethyl imidazo[5,1-b]thiazol-3-yl)-6-((1R)-1-hydroxyethyl)-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 12069981(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(3-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylic Acid収率 56.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 157.3 mg of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(3-methylimidazo[5,1-b]thiazol-2-yl)-1-carbapen-2-em-3-carboxylate in 3 ml of THF and 3 ml of {fraction (1/15)} M phosphate buffer (pH 6.8) was added 0.24 g of 100 Pd-C. The reactor was purged with hydrogen, the reaction mixture was stirred at room temperature for 1 hour. The catalyst was collected by filtration, and washed with 50 ml of water. The filtrate was diluted with 20 ml of ethyl acetate, separated, and the organic layer was further washed with water. The combined aqueous layer was concentrated under reduced pressure to a volume of about 30 ml. The residual concentrate was purified by column chromatography on DIAION HP-20. The fraction containing the aimed product was lyophilized to give 63.5 mg of the title compound.

後処理

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration
  3. washwashed with 50 ml of water
  4. additionThe filtrate was diluted with 20 ml of ethyl acetate
  5. customseparated
  6. washthe organic layer was further washed with water
  7. concentrationThe combined aqueous layer was concentrated under reduced pressure to a volume of about 30 ml
  8. concentrationThe residual concentrate
  9. customwas purified by column chromatography on DIAION HP-20
  10. additionThe fraction containing the aimed product

出典と根拠

ORDレコード
ord-71a5d7e4618e4b8dab7e152463bf2d82
出典データセット
uspto-grants-2001_10
特許番号
US06310056B1

反応ノート

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