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Methanol → 1-Tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl ester

HRID 2405815
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2405815
[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH:6]1[CH2:8][CH2:9]SC)=[O:4].O[O:21][S:22]([O-:24])=O.[K+].[CH3:26]O>O>[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:7][CH:6]1[CH2:8][CH2:9][S:22]([CH3:26])(=[O:24])=[O:21])=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 686167901-Tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)cyclopropanecarboxylic acid methyl ester

Produkt 1

HCID 686187851-Tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A solution of 1-tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)-cyclopropanecarboxylic acid methyl ester (0.63 g, 2.2 mmol) in 10 mL MeOH was added slowly to a suspension of Oxone (2.0 g, 3.3 mmol) in 10 mL H2O at rt. After 2 h at it, the solvent was removed in vacuo and the residue was taken up in EtOAc and H2O (15 mL each). The aqueous layer was extracted with 3×10 mL EtOAc. The combined organics were washed with brine and dried over anhydrous MgSO4. Following concentration in vacuo, the residue was purified by column chromatography on SiO2 (0→65% EtOAc/hexanes) to produce 1-tert-butoxycarbonylamino-2-(2-methanesulfonylethyl)-cyclopropanecarboxylic acid methyl ester (0.50 g, 71%) as a colorless film. LCMS found 222.0 [(M-Boc)+H]+.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. extractionThe aqueous layer was extracted with 3×10 mL EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentration in vacuo
  6. customthe residue was purified by column chromatography on SiO2 (0→65% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cbdbaa1bd3784e6d9a4655d701d357d6
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809267B2

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