Tetrahydrofuran → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 573008

Reaktionsgleichung

Reaktionsgleichung von HRID 573008
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17](N(OC)C)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.S([O-])(O)(=O)=O.[K+]>CC1CCCO1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:17]=[O:18])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 516920Potassium bisulfateHCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 73012-MethyltetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1090 mg (3.5 mmol) Nα-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-phenylalanine-amide was dissolved in 20 mL 2-methyltetrahydrofuran and cooled to 0° C. Then 4.2 mL (4.2 mmol) of a 1M lithium aluminum hydride solution was added slowly to THF, and the reaction mixture was stirred for 30 min at 0° C. Next 5% aqueous potassium hydrogen sulfate solution was added cautiously. The batch was then diluted with water and extracted with MTBE. The organic phase was dried over magnesium sulfate and concentrated in vacuo, yielding 820 mg (94% of the theoretical) of the title compound.

Aufarbeitung

  1. extractionextracted with MTBE
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f81bbe8e7a53400187c1f199d5bbf0ab
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029406B2

Verknüpfte Notizen

Wird geladen…