Tributylphosphine → ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl) [(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

HRID 508075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508075
O[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3([OH:24])[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)=[CH:11][C:10]=2[CH3:25])[CH:6]=[CH:7][CH:8]=1.[F:26][C:27]1[CH:32]=[C:31]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N+:43]([O-:45])=[O:44])(=[O:36])=[O:35])[CH:30]=[CH:29][C:28]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:26][C:27]1[CH:32]=[C:31]([N:33]([CH2:2][C:3]2[CH:4]=[C:5]([C:9]3[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]4([OH:24])[CH2:19][CH2:20][S:21][CH2:22][CH2:23]4)=[CH:11][C:10]=3[CH3:25])[CH:6]=[CH:7][CH:8]=2)[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[N+:43]([O-:45])=[O:44])(=[O:35])=[O:36])[CH:30]=[CH:29][C:28]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 231571864-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-olHCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Produkt 1

HCID 23157627ethyl 3-(2-fluoro-4-{({4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-yl}methyl) [(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-({[3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol (0.90 g, 2.51 mmol), ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (1.05 g, 2.64 mmol) and tributylphosphine (0.86 mL, 3.26 mmol) in tetrahydrofuran (15 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.85 g, 3.26 mmol) under stirring at room temperature, and the mixture was stirred for 10 hr. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (1.71 g, yield 92%) as a pale-yellow amorphous powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 10 hr
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-2c32ec83a7794e8a962bf80857442f8c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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