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 2246103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246103
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]

Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cebe32cd12824013a5ac3114882d13b3
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687490B2

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