Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate → (8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one

HRID 2040012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040012
[CH:1]([C@@H:4]1[NH:18][C:17](=[O:19])[C@H:16]([NH:20]C(=O)OCC2C=CC=CC=2)[CH2:15][C:14]2=[CH:31][N:11]([CH:12]=[N:13]2)[CH2:10][CH:9]=[CH:8][CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2]>CO.[Pd]>[NH2:20][C@@H:16]1[CH2:15][C:14]2=[CH:31][N:11]([CH:12]=[N:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([CH:1]([CH3:2])[CH3:3])[NH:18][C:17]1=[O:19]

Komponenten

4

Edukt 1

HCID 86655968Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate

Produkt 1

HCID 67028858(8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-oneAusbeute 17,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 0.49 g (1.14 mmol) of benzyl ((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate from step C in 80 ml of methanol was hydrogenated over 0.12 g of palladium on carbon (10%) under a hydrogen atmosphere under autogenous pressure at RT. After the starting material had completely reacted, the mixture was filtered and concentrated. The residue was purified by preparative HPLC. 0.06 g of the title compound was obtained.

Aufarbeitung

  1. customAfter the starting material had completely reacted
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a5bd3d4ade8949f7a077fe6a7b5828bd
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580777B2

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