Hydrochloric Acid → 3-{4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid

HRID 658299

Reaktionsgleichung

Reaktionsgleichung von HRID 658299
C[O:2][C:3](=[O:42])[CH2:4][CH2:5][NH:6][C:7](=[O:41])[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH2:38][CH:39]=[CH2:40])([CH2:18][O:19][C:20]2[CH:25]=[C:24]([CH3:26])[C:23]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[C:22]([CH3:37])[CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:10][CH:9]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:15]([C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:42])=[O:2])=[O:41])=[CH:13][CH:12]=1)([CH2:18][O:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[C:22]([CH3:37])[CH:21]=1)[CH2:38][CH:39]=[CH2:40])[CH:16]=[CH2:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 674863613-{4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester

Produkt 1

HCID 167504293-{4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acidAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-{4-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoylamino}-propionic acid methyl ester (0.0438 g, 0.0756 mmol) in THF (1.0 mL) is treated with 1N LiOH (1.0 mL) and stirred overnight at room temperature. The reaction mixture is acidified with 1N HCl (1.1 mL), diluted with water (5 mL), and extracted with EtOAc (3×10 mL). The combined extracts are dried over MgSO4, filtered, and concentrated to provide 0.0105 g (24%) of the title compound as a white solid. MS (ES): 566.4 [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-3360dae275ae4fbf99cdf374998fc2f5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076374B2

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