Trisodium Phosphate → Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1799702ノート

反応式

HRID 1799702 の反応式
P([O-])([O-])([O-])=O.[Na+:6].[Na+].[Na+].[OH:9][C@@H:10]([C@H:12]1[C:42](=[O:43])[N:14]2[C:15]([C:29]([O:31]CC3C=CC([N+]([O-])=O)=CC=3)=[O:30])=[C:16]([S:19]/[CH:20]=[CH:21]\[C:22]3[S:26][CH:25]=[N:24][C:23]=3[CH2:27][OH:28])[C@H:17]([CH3:18])[C@H:13]12)[CH3:11]>C1COCC1.[Pd]>[OH:9][C@@H:10]([C@H:12]1[C:42](=[O:43])[N:14]2[C:15]([C:29]([O-:31])=[O:30])=[C:16]([S:19]/[CH:20]=[CH:21]\[C:22]3[S:26][CH:25]=[N:24][C:23]=3[CH2:27][OH:28])[C@H:17]([CH3:18])[C@H:13]12)[CH3:11].[Na+:6]

参加物

5

反応物 2

HCID 24243Trisodium PhosphateHCID 694700964-Nitrobenzyl (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 23676797Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

10% Pd—C (hydrous, water content 53%) (1.42 g) was added to a solution of 40 ml of a 1/15 M sodium phosphate buffer solution (pH 6.8) of 957 mg of 4-nitrobenzyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate in 40 ml of THF, and the mixture was stirred under a hydrogen atmosphere for 1.5 hr. The 10% Pd—C was removed by filtration and was washed with water. The filtrate was adjusted to pH 6.6 by the addition of saturated sodium bicarbonate water, followed by washing with 40 ml of ethyl acetate. The aqueous layer was concentrated to about 5 ml, and the concentrate was purified by column chromatography (2% methanol-water) on Cosmosil 40C18-PREP to give 360 mg of the title compound.

後処理

  1. customThe 10% Pd—C was removed by filtration
  2. washwas washed with water
  3. additionThe filtrate was adjusted to pH 6.6 by the addition of saturated sodium bicarbonate water
  4. washby washing with 40 ml of ethyl acetate
  5. concentrationThe aqueous layer was concentrated to about 5 ml
  6. customthe concentrate was purified by column chromatography (2% methanol-water) on Cosmosil 40C18-PREP

出典と根拠

ORDレコード
ord-dafaa43b2ab9471aa57a5cda563386e7
出典データセット
uspto-grants-2013_01
特許番号
US08344154B2

反応ノート

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