Water → N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-fluoro-1-naphthalenecarboxamide

HRID 1610460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610460
[NH2:1][CH:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8](OC2C=CC=CC=2)=[CH:7][CH:6]=1)[OH:4].[F:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C:40]([OH:42])=O)=[CH:32][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C.ON1[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=2N=N1.[OH2:65]>C(#N)C>[OH:4][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:65][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:6]=1)[CH:2]([NH:1][C:40]([C:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:30]([F:29])=[CH:31][CH:32]=1)=[O:42])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=1

Komponenten

7

Edukt 5

HCID 962WaterHCID 684484-Fluoro-1-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22261609(1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol

Produkt 1

HCID 22262079N-((1RS,2SR)-2-hydroxy-2-(3-phenoxyphenyl)-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-4-fluoro-1-naphthalenecarboxamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (400 mg, 1.03 mmol) in acetonitrile (30 ml) were added 4-fluoronaphthalenecarboxylic acid (196 mg, 1.03 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (247 mg, 1.55 mmol) and 1-hydroxy-1H-benzotriazole (158 mg, 1.03 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. Recrystallization of the residue from ethyl acetate-hexane gave the title compound (446 mg, 77%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed successively with 1N hydrochloric acid, 1N aqueous sodium hydroxide solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customRecrystallization of the residue from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9248ae2fe9f04abbb0a36939d61eb283
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

Notizen zur Reaktion

Wird geladen…