Triphenylphosphine → Ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate

HRID 508093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508093
[F:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[C:28]1([C:34]2[N:35]=[C:36]([CH2:39][CH:40]([C:44]3[CH:49]=[CH:48][C:47]([CH2:50]O)=[CH:46][CH:45]=3)[CH2:41][CH2:42][CH3:43])[S:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([N:8]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[CH2:50][C:47]2[CH:48]=[CH:49][C:44]([CH:40]([CH2:39][C:36]3[S:37][CH:38]=[C:34]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:35]=3)[CH2:41][CH2:42][CH3:43])=[CH:45][CH:46]=2)[CH:5]=[CH:4][C:3]=1[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23143323(4-{1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]butyl}phenyl)methanolHCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Produkt 1

HCID 23157210Ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.686 g, 1.73 mmol), (4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}phenyl)methanol (0.389 g, 1.15 mmol) and triphenylphosphine (0.603 g, 2.30 mmol) in tetrahydrofuran (15 mL) was stirred under ice-cooling, and diethyl azodicarboxylate (40% toluene solution, 1.05 mL, 2.3 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 16 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give ethyl 3-{2-fluoro-4-[[(2-nitrophenyl)sulfonyl](4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate as a yellow oil. To a solution of the obtained oil and mercaptoacetic acid (0.291 g, 3.16 mmol) in N,N-dimethylformamide (15 mL) was added lithium hydroxide monohydrate (0.265 g, 6.32 mmol), and the mixture was stirred at room temperature for 2 hr. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (0.420 g, yield 69%, 2 steps) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d22e85ce7eb3459ca87f2effc9a675a7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

Notizen zur Reaktion

Wird geladen…