Ethyl Acetate → (S)-tert-butyl 1-oxo-1-phenylpentan-2-ylcarbamate

HRID 13104

Reaktionsgleichung

Reaktionsgleichung von HRID 13104
CON(C)[C:4](=[O:17])[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][CH2:7][CH3:8].[C:19]1([Mg]Br)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[O:17]=[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:6][CH2:7][CH3:8]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 9992774(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamateHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 59339674(S)-tert-butyl 1-oxo-1-phenylpentan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a 50 mL round-bottomed flask was (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopentan-2-ylcarbamate (91d, 250 mg, 0.96 mmol) dissolved in THF (9.6 ml). Phenylmagnesium bromide (2.88 ml, 2.88 mmol) 1.0 M in THF was added. The reaction was stirred at r.t. for 5 h. The reaction was poured into a mixture of saturated ammonium chloride and ethyl acetate. The mixture was shaken and the layers separated. The water layer was washed twice with ethyl acetate. The combined organic layers were washed once with a small portion of water and dried over sodium sulphate. The solvent was evaporated and the crude product was purified by flash chromatography.

Aufarbeitung

  1. customIn a 50 mL round-bottomed flask was
  2. stirringThe mixture was shaken
  3. customthe layers separated
  4. washThe water layer was washed twice with ethyl acetate
  5. washThe combined organic layers were washed once with a small portion of water
  6. dry with materialdried over sodium sulphate
  7. customThe solvent was evaporated
  8. customthe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1ba14a93921b47a5b43504fa8549e008
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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