Hydrochloric Acid → 3-{4-[1-Propyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-butyl]-benzoylamino}-propionic acid

HRID 658302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658302
C[O:2][C:3](=[O:40])[CH2:4][CH2:5][NH:6][C:7](=[O:39])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH2:36][CH:37]=[CH2:38])([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:10][CH:9]=1.[Li+].[OH-].Cl>C1COCC1>[CH2:15]([C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:40])=[O:2])=[O:39])=[CH:13][CH:12]=1)([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:34])([F:35])[F:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1)[CH2:36][CH2:37][CH3:38])[CH2:16][CH3:17]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 674857653-{4-[1-Allyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester

Produkt 1

HCID 247650483-{4-[1-Propyl-1-(4'-trifluoromethyl-biphenyl-4-yloxymethyl)-butyl]-benzoylamino}-propionic acidAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-{4-[1-allyl-1-(4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester (0.0703 g, 0.120 mmol) in THF (2.0 mL) is treated with 1N LiOH (2.0 mL) and stirred overnight at room temperature. The reaction mixture is acidified with 1N HCl (2.2 mL) and extracted with EtOAc (3×10 mL). The combined extracts are dried over MgSO4, filtered, and concentrated to provide 0.0401 g, (58%) of the title compound as a white solid. MS (ES): 570.4 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialThe combined extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b32bf2fc0ca249e6b37df66312bcbe32
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076374B2

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