Diethyl Ether → N-(tert-butoxycarbonyl)-N-(2-oxopropyl)glycine

HRID 2109838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109838
[C:1]([O:5][C:6]([N:8]([CH:13](OC)[C:14](=[O:17])NC)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][Mg]Br.CCOCC>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14](=[O:17])[CH3:20])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 86602785N-[(tert-butoxy)carbonyl]-N-[(methoxy)-(methyl)carbamoylmethyl]glycineHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 57634645N-(tert-butoxycarbonyl)-N-(2-oxopropyl)glycine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of N-[(tert-butoxy)carbonyl]-N-[(methoxy)-(methyl)carbamoylmethyl]glycine (1.0 g, 3.6 mmol; Helvetica Chimica Acta 2000, 83 1825), in anhydrous THF (30 mL) under an atmosphere of nitrogen, a solution of methyl magnesium bromide in ether (2.6 mL, 3M, 7.8 mmol) was added. The reaction mixture was stirred at room temperature for 1 h, cooled back to 0° C., quenched with aqueous HCl, and diluted with ether. The organic extract was washed with brine (pH adjusted to ˜4-5 with addition of aqueous sodium hydroxide), dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound.

Aufarbeitung

  1. temperaturecooled back to 0° C.
  2. customquenched with aqueous HCl
  3. additiondiluted with ether
  4. extractionThe organic extract
  5. washwas washed with brine (
  6. additionpH adjusted to ˜4-5 with addition of aqueous sodium hydroxide),
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-02cba4e4cff1485db8d137cb71700b45
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517532B2

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