Tributylphosphine → N-[(2S)-2-fluoropropyl]-N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide

HRID 1879406

Reaktionsgleichung

Reaktionsgleichung von HRID 1879406
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH:14][S:15]([C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)(=[O:17])=[O:16].C(P(CCCC)CCCC)CCC.[F:37][C@@H:38]([CH3:41])[CH2:39]O.N(/C(N1CCCCC1)=O)=N\C(N1CCCCC1)=O>C1COCC1>[F:37][C@@H:38]([CH3:41])[CH2:39][N:14]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][C:5]=1[O:4][CH2:3][O:2][CH3:1])[CH2:11][CH2:10][CH2:9]2)[S:15]([C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)(=[O:17])=[O:16]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 5702657diazenedicarboxylic acid bis(N,N-piperidide)HCID 11528331(2S)-2-fluoropropan-1-olHCID 58398543N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide

Produkt 1

HCID 58398425N-[(2S)-2-fluoropropyl]-N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamideAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

896 mg of N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide, 665 mg of tributyl phosphine, and 257 mg of (2S)-2-fluoropropan-1-ol were dissolved in 8.96 mL of THF, and 829 mg of 1,1′-[(E)-diazen-1,2-diyldicarbonyl]dipiperidine was added thereto, followed by stirring overnight at room temperature. After the insoluble materials were removed by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50) to obtain 632 mg of N-[(2S)-2-fluoropropyl]-N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide.

Aufarbeitung

  1. customAfter the insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-35ad8660e8664d61bd5bd05f70e8665a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314240B2

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