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Phosphate → (1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester

HRID 465339
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 465339
[Na+].[CH3:2][N:3]1[CH2:7][C@H:6]([S:8][C:9]2[C@H:10]([CH3:23])[C@@H:11]3[C@@H:18]([C@H:19]([OH:21])[CH3:20])[C:17](=[O:22])[N:12]3[C:13]=2[C:14]([O-:16])=[O:15])[CH2:5][C:4]1=[S:24].C(=O)([O-])[O-].[K+].[K+].[C:31]([O:34][CH2:35]I)(=[O:33])[CH3:32].P([O-])([O-])([O-])=O>CN(C)C=O>[C:31]([O:34][CH2:35][O:15][C:14]([C:13]1[N:12]2[C:17](=[O:22])[C@H:18]([C@H:19]([OH:21])[CH3:20])[C@H:11]2[C@@H:10]([CH3:23])[C:9]=1[S:8][C@H:6]1[CH2:7][N:3]([CH3:2])[C:4](=[S:24])[CH2:5]1)=[O:16])(=[O:33])[CH3:32]
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Komponenten

6

Edukt 4

HCID 1061PhosphateHCID 11430Potassium CarbonateHCID 11820084Iodomethyl acetateHCID 131717556(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt

Produkt 1

HCID 131717555
(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester
Ausbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt (400 mg) is suspended in N,N-dimethylformamide (5 ml), and thereto is added potassium carbonate (146 mg). To the mixture is added acetoxymethyl iodide (275 mg) at 5°-7° C., and the mixture is stirred at the same temperature for one hour. The reaction mixture is poured into phosphate buffer (pH 7.0) and extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated to dryness under reduced pressure. The residue is purified by silica gel column chromatography (eluent, chloroform - chloroform:ethanol=98:2), followed by crystallization from tetrahydrofuran and diethyl ether to give (1R, 5S, 6S)-2-[(4R)-N-methylpyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid acetoxymethyl ester (250 mg) as colorless needles.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent, chloroform - chloroform:ethanol=98:2)
  6. customfollowed by crystallization from tetrahydrofuran and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4f28a8d08fae45c0b1fc84c289a6d0b6
Quelldatensatz
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05153187

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