Sodium methanethiolate → 1-Tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)cyclopropanecarboxylic acid methyl ester

HRID 2405814

Reaktionsgleichung

Reaktionsgleichung von HRID 2405814
[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][CH:6]1[CH2:8][CH2:9]OS(C)(=O)=O)=[O:4].[CH3:23][S-:24].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:7][CH:6]1[CH2:8][CH2:9][S:24][CH3:23])=[O:4]

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 574451671-Tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester

Produkt 1

HCID 686167901-Tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)cyclopropanecarboxylic acid methyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 1-tert-butoxycarbonylamino-2-(2-methanesulfonyloxyethyl)cyclopropanecarboxylic acid methyl ester (0.52 g, 1.53 mmol) in 5 mL MeOH was added dropwise to a rt solution of sodium thiomethoxide in 3 mL MeOH. After 4.75 h, 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, 1-tert-butoxycarbonylamino-2-(2-methylsulfanylethyl)cyclopropanecarboxylic acid methyl ester (0.350 g, 79%) was obtained as a colorless oil that was used without further purification. LCMS found 312.0 [M+Na]+.

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

Quellen und Nachweise

ORD-Eintrag
ord-509f9e19ac314d43987b3989195b46a2
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809267B2

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