1,1-Dimethylethyl N-[(3S)-2,2-dimethyl-4-oxo-1-(phenylmethoxy)-3-azetidinyl]carbamate → HCID 14010104, Verbindung

HRID 1788788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788788
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12]([CH3:14])([CH3:13])[N:11]([O:15]CC2C=CC=CC=2)[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12]([CH3:14])([CH3:13])[N:11]([OH:15])[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 1

HCID 140101021,1-Dimethylethyl N-[(3S)-2,2-dimethyl-4-oxo-1-(phenylmethoxy)-3-azetidinyl]carbamate

Produkt 1

HCID 14010104HCID 14010104, VerbindungAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 14.77 g (0.0461 mole) of (3S)-3-[(t-butyloxycarbonyl)amino]-4,4-dimethyl-1-(phenylmethoxy)-2-azetidinone in 15 ml of ethanol and 85 ml of ethyl acetate was hydrogenated over 0.75 g of 5% palladium-on-carbon catalyst for 1.5 hours at 1 atmosphere. The reaction mixture was filtered and concentrated to give a white solid. Recrystallization from ethyl acetate gave 8.82 g of the title compound, melting point 148°-149° C., [α]D =+31° (C =1, ethyl acetate).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto give a white solid
  4. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b8abfc5399164ec0b2d27d6533f14659
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04684722

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