Tributylphosphine → HCID 58398388, Verbindung

HRID 1879413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879413
[F:1][C@@H:2]([CH3:24])[CH2:3][N:4]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[OH:23])[CH2:19][CH2:18][CH2:17]2)[S:5]([C:8]1[S:9][CH:10]=[C:11]([CH3:13])[N:12]=1)(=[O:7])=[O:6].C(P(CCCC)CCCC)CCC.O[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[N:44][CH:45]=1.N(/C(N1CCCCC1)=O)=N\C(N1CCCCC1)=O>C1COCC1>[F:1][C@@H:2]([CH3:24])[CH2:3][N:4]([S:5]([C:8]1[S:9][CH:10]=[C:11]([CH3:13])[N:12]=1)(=[O:7])=[O:6])[C:14]1[CH:15]=[C:16]2[C:20]([CH2:19][CH2:18][CH2:17]2)=[CH:21][C:22]=1[O:23][CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([O:48][CH2:49][CH3:50])=[O:47])=[N:44][CH:45]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 13518564Ethyl 5-(hydroxymethyl)pyridine-2-carboxylateHCID 58398469N-[(2S)-2-fluoropropyl]-N-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-2-sulfonamide

Produkt 1

HCID 58398388HCID 58398388, VerbindungAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

133 mg of N-[(2S)-2-fluoropropyl]-N-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-4-methyl-1,3-thiazole-2-sulfonamide, 94.4 mg of tributylphosphine, and 71.5 mg of ethyl 5-(hydroxymethyl)pyridine-2-carboxylate were dissolved in 1.33 mL of THF, and 118 mg of 1,1′-[(E)-diazene-1,2-diyldicarbonyl]dipiperidine was added thereto, followed by stirring overnight at room temperature. After the insoluble materials were removed by filtration, the solvent was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to obtain 116 mg of ethyl 5-{[(6-{[(2S)-2-fluoropropyl][(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino}-2,3-dihydro-1H-inden-5-yl)oxy]methyl}pyridine-2-carboxylate.

Aufarbeitung

  1. customAfter the insoluble materials were removed by filtration
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Quellen und Nachweise

ORD-Eintrag
ord-4b90824504ac4b23bb65fa8237d162ed
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314240B2

Notizen zur Reaktion

Wird geladen…