Piperidine → (13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

HRID 2040002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040002
[CH:1]([C@@H:4]1[NH:23][C:22](=[O:24])[C@H:21]([NH:25]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH2:20][C:19]2=[CH:43][CH:44]=[C:16]([CH:17]=[CH:18]2)[O:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2].N1CCCCC1>CO.[Pd]>[NH2:25][C@@H:21]1[CH2:20][C:19]2=[CH:18][CH:17]=[C:16]([CH:44]=[CH:43]2)[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([CH:1]([CH3:2])[CH3:3])[NH:23][C:22]1=[O:24]

Komponenten

5

Edukt 2

HCID 8082PiperidineHCID 866559669H-Fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamate

Produkt 1

HCID 67028556(13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 0.87 (1.46 mmol) of 9H-fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)-carbamate and 0.16 g of 10% Pd/C in 100 ml of methanol was stirred under a hydrogen atmosphere at RT. After stirring overnight and addition of 0.5 ml of piperidine, stirring was continued for 2 h, and the mixture was filtered and freed of solvent. The residue was separated by preparative HPLC. The required fractions were combined and freeze dried. 0.18 g of the title compound was obtained as trifluoroacetate.

Aufarbeitung

  1. stirringAfter stirring overnight
  2. stirringstirring
  3. filtrationthe mixture was filtered
  4. customThe residue was separated by preparative HPLC
  5. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-7e0f46dbe4aa48639fae20aeb0c53f53
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580777B2

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