Dimethylformamide → (1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester

HRID 465337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465337
[K+].[NH:2]1[CH2:6][C@H:5]([S:7][C:8]2[C@H:9]([CH3:22])[C@@H:10]3[C@@H:17]([C@H:18]([OH:20])[CH3:19])[C:16](=[O:21])[N:11]3[C:12]=2[C:13]([O-:15])=[O:14])[CH2:4][C:3]1=[S:23].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[C:35]([O:40][CH2:41]I)(=[O:39])[CH:36]([CH3:38])[CH3:37]>C(OCC)(=O)C>[C:35]([O:40][CH2:41][O:14][C:13]([C:12]1[N:11]2[C:16](=[O:21])[C@H:17]([C@H:18]([OH:20])[CH3:19])[C@H:10]2[C@@H:9]([CH3:22])[C:8]=1[S:7][C@H:5]1[CH2:6][NH:2][C:3](=[S:23])[CH2:4]1)=[O:15])(=[O:39])[CH:36]([CH3:38])[CH3:37]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10376456Iodomethyl 2-methylpropanoateHCID 131717553(1R, 5S, 6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid potassium salt

Produkt 1

HCID 9955020(1R,5S,6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl esterAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of (1R, 5S, 6S)-2-[(4R)-pyrrolidine-2- thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2- em-3-carboxylic acid potassium salt (0.34 g), N,N-dimethylformamide (3 ml) and potassium carbonate (0.12 g) is added dropwise isobutyryloxymethyl iodide (0.27 g) under ice cooling. After stirring the mixture at the same temperature for 30 minutes, ethyl acetate (10 ml) is added to the reaction mixture, and the mixture is washed with water, and the organic layer is dried and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel flash column chromatography (eluent, chloroform: ethanol=20:1), followed by crystallization from isopropyl ether and ethyl acetate to give (1R, 5S, 6S)-2-[(4R)-pyrrolidine-2-thion-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid isobutyryloxymethyl ester (0.12 g) as colorless needles.

Aufarbeitung

  1. washthe mixture is washed with water
  2. customthe organic layer is dried
  3. customevaporated under reduced pressure
  4. customto remove the solvent
  5. customThe residue is purified by silica gel flash column chromatography (eluent, chloroform: ethanol=20:1)
  6. customfollowed by crystallization from isopropyl ether and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0077f6b3fd504099ae3ffac10bcbd483
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153187

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