Sodium Iodide → 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

HRID 1799701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799701
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[SH:10].C1(P(O[C:26]2[C@H:27]([CH3:50])[C@@H:28]3[C@@H:45]([C@H:46]([OH:48])[CH3:47])[C:44](=[O:49])[N:29]3[C:30]=2[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=2)=[O:32])(C2C=CC=CC=2)=O)C=CC=CC=1.[I-].[Na+].C(OCC)(=O)C>CC(C)=O.[Cl-].[Na+].O.[Ag]>[OH:48][C@@H:46]([C@H:45]1[C:44](=[O:49])[N:29]2[C:30]([C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][C:38]([N+:41]([O-:43])=[O:42])=[CH:39][CH:40]=3)=[O:32])=[C:26]([S:10]/[CH:9]=[CH:8]\[C:7]3[S:6][CH:5]=[N:4][C:3]=3[CH2:2][OH:1])[C@H:27]([CH3:50])[C@H:28]12)[CH3:47]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 15871605p-nitrobenzyl (1R,5R,6S)-2-(di-phenylphosphoryloxy)-6-[(R)-1-hydroxyethyl]-1-methyl-carbapen-2-em-3-carboxylateHCID 875108504-Hydroxymethyl-5-[(z)-2-mercaptoethen-1-yl]thiazole

Produkt 1

HCID 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-carboxylateAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23954SilverKatalysatorHCID 180AcetoneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

The crude crystal of the silver salt of 4-hydroxymethyl-5-[(Z)-2-mercaptoethen-1-yl]thiazole (283 mg) was added to 10 ml of a solution of 599 mg of 4-nitrobenzyl (1R,5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate in dry acetone under an argon atmosphere at 4° C., and 303 mg of sodium iodide was added thereto. The mixture was stirred at the same temperature for 18 hr. Ethyl acetate (20 ml) and 20 ml of semi-saturated brine were added thereto, and the mixture was filtered through Celite and was washed with ethyl acetate. The filtrate was separated, the organic layer was washed with semi-saturated brine, was dried over anhydrous magnesium sulfate, and was filtered, and ethyl acetate was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to give 298 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.

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. washwas washed with ethyl acetate
  3. customThe filtrate was separated
  4. washthe organic layer was washed with semi-saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationwas filtered
  7. customethyl acetate was removed by distillation under the reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-bacfc7537f4a410caf111736a06bc418
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344154B2

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