(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate → tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

HRID 1098776

Reaktionsgleichung

Reaktionsgleichung von HRID 1098776
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11](N(OC)C)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[Mg][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1>C1COCC1>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([C:11](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:10])[CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178490745HCID 178490745, Verbindung

Produkt 1

HCID 59339682tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (777 mg, 3.3 mmol) in dry THF (50 ml) was added a solution of bromo(3-methoxyphenyl)magnesium (1M in THF, 10 ml, 10 mmol). The mixture was stirred at r.t. for 5 h, then quenched with saturated aqueous NH4Cl (50 ml). After stirring for 30 min, the layers were separated, the aqueous layer extracted with ethyl acetate (50 ml). The combined organic layers were dried with Na2SO4, and the solvent was removed in vacuo. The subtitle compound was isolated by flash chromatography on silica gel (n-heptane/ethyl acetate, gradient from 20 to 50% ethyl acetate). Yield 471 mg (94%).

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl (50 ml)
  2. stirringAfter stirring for 30 min
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate (50 ml)
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a685ec89ad42407281c0502c66b3da02
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143290B2

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