HCID 86602935, Verbindung → HCID 59699536, Verbindung

HRID 901791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901791
C([O:8][C@@H:9]1[C@@H:40]([O:41]CC2C=CC=CC=2)[C@H:39]([O:49][C@H:50]2[O:79][C@H:78]([CH3:80])[C@@H:69]([O:70]CC3C=CC=CC=3)[C@H:60]([O:61]CC3C=CC=CC=3)[C@H:51]2[O:52]CC2C=CC=CC=2)[C@@H:38]([CH2:81][O:82]CC2C=CC=CC=2)[O:37][C@@H:10]1[O:11][C@H:12]1[C@H:16]([F:17])[CH2:15][N:14](C(OCC2C=CC=CC=2)=O)[C@@H:13]1[CH2:28][O:29]CC1C=CC=CC=1)C1C=CC=CC=1>CO.Cl.[OH-].[Pd+2].[OH-].[C]>[C@H:50]1([O:49][C@@H:39]2[C@@H:38]([CH2:81][OH:82])[O:37][C@H:10]([O:11][C@H:12]3[C@H:16]([F:17])[CH2:15][NH:14][C@@H:13]3[CH2:28][OH:29])[C@H:9]([OH:8])[C@H:40]2[OH:41])[O:79][C@H:78]([CH3:80])[C@@H:69]([OH:70])[C@H:60]([OH:61])[C@H:51]1[OH:52]

Komponenten

4

Edukt 1

HCID 86602935HCID 86602935, Verbindung

Produkt 1

HCID 59699536HCID 59699536, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178502593HCID 178502593, VerbindungKatalysatorHCID 21893726Hydrochloride methanolLösungsmittel

Versuchsvorschrift

The compound (109 mg, 90.2 μmol) synthesized in Example 9 (9d) was dissolved in 1% hydrochloric acid methanol solution (5 mL) and 20% palladium hydroxide-carbon (55 mg) was added thereto, followed by stirring of the mixture under a hydrogen atmosphere for 1 hour. After the catalyst was removed by celite filtration, 28% ammonia water (0.2 mL) was added thereto and the mixture was stirred for 10 minutes. After the solvent was distilled off under reduced pressure and it was passed through ion exchange resin (Dowex 50w×8) column with water (30 mL), 1% ammonia water (30 mL) was flowed through. The ammonia water containing the desired compound was concentrated under reduced pressure and the residue was purified using silica gel flash column chromatography (ethyl acetate:methanol:water, 5:2:1-1:1:1, V/V) to obtain the desired title compound (26 mg, 65%) as a colorless solid.

Aufarbeitung

  1. customAfter the catalyst was removed by celite filtration, 28% ammonia water (0.2 mL)
  2. additionwas added
  3. stirringthe mixture was stirred for 10 minutes
  4. distillationAfter the solvent was distilled off under reduced pressure and it
  5. concentrationThe ammonia water containing the desired compound was concentrated under reduced pressure
  6. customthe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-82480500b0c642e096569d8ed65e5991
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361744B2

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