HCID 53918863, Verbindung → HCID 14257300, Verbindung

HRID 653259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653259
C(O[C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C.[Na].[C:31]([O:35][CH3:36])(=[O:34])[CH2:32][SH:33]>CO>[CH3:36][O:35][C:31]([CH2:32][S:33][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:34]

Komponenten

4

Edukt 2

HCID 53918863HCID 53918863, VerbindungHCID 86741499HCID 86741499, Verbindung

Produkt 1

HCID 14257300HCID 14257300, VerbindungAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1.93 g of (3S,4S)-4-acetoxy-3-tritylamino-2-oxoazetidine in 100 ml of methanol is added a solution of 0.64 g of methyl thioglycolate sodium salt with stirring under ice-cooling. After 1 hour, the solvent is distilled off and the residue is dissolved in ethyl acetate. The solution is washed with water, then the solvent is distilled off, and the residue is purified by silica gel column-chromatography (methylene chloride: ethyl acetate=11:1) to give 1.38 g of (3R,4R)-4-methoxycarbonylmethylthio-3-tritylamino-2-oxoazetidine (A) and 0.92 g of the corresponding (3R,4S)-isomer (B)

Aufarbeitung

  1. temperaturecooling
  2. distillationthe solvent is distilled off
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe solution is washed with water
  5. distillationthe solvent is distilled off
  6. customthe residue is purified by silica gel column-chromatography (methylene chloride: ethyl acetate=11:1)

Quellen und Nachweise

ORD-Eintrag
ord-d6ad74a55cf04d949688fbb507613d3c
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675397

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