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9H-Fluoren-9-ylmethyl ((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)carbamate → (9S,12R)-12-Amino-9-isopropyl-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-11-one

HRID 626627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626627
C1C2C(COC(=O)[NH:17][C@@H:18]3[CH2:33][C:32]4=[CH:34][CH:35]=[C:29]([CH:30]=[CH:31]4)[O:28][CH2:27][CH:26]=[CH:25][CH2:24][O:23][CH2:22][C@H:21]([CH:36]([CH3:38])[CH3:37])[NH:20][C:19]3=[O:39])C3C(=CC=CC=3)C=2C=CC=1>CO.[Pd]>[NH2:17][C@@H:18]1[CH2:33][C:32]2=[CH:31][CH:30]=[C:29]([CH:35]=[CH:34]2)[O:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][CH2:22][C@H:21]([CH:36]([CH3:37])[CH3:38])[NH:20][C:19]1=[O:39]
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Komponenten

4

Edukt 1

HCID 683028049H-Fluoren-9-ylmethyl ((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)carbamate

Produkt 1

HCID 58360483(9S,12R)-12-Amino-9-isopropyl-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-11-oneAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6.82 g (12.62 mmol) of 9H-fluoren-9-ylmethyl((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),4,14(18),15-tetraen-12-yl)-carbamate and 4.4 g of 10% Pd/C in 880 ml of methanol was stirred under a hydrogen atmosphere at RT. After 6 h, it was filtered and freed of solvent. The residue was separated by preparative HPLC. The required fractions were combined, acetonitrile was evaporated off, and the resulting aqueous solution was made slightly alkaline with sodium bicarbonate. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were dried over sodium sulfate, filtered and concentrated. Chromatography on silica gel with ethyl acetate/methanol mixtures afforded the title compound (2.90 g).

Aufarbeitung

  1. filtrationit was filtered
  2. customThe residue was separated by preparative HPLC
  3. customacetonitrile was evaporated off
  4. extractionThe aqueous phase was extracted several times with ethyl acetate
  5. dry with materialthe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b564ea9e745d4ba19ed4d95f56607297
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309207B2

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