Hydrochloric Acid → Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoate

HRID 2422317

Reaktionsgleichung

Reaktionsgleichung von HRID 2422317
[CH:1]([C:4]1[N:5]=[C:6]([NH:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:18][C:19]1[CH:38]=[CH:37][C:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.Cl>O.CN(C)C=O>[CH:1]([C:4]1[N:5]=[C:6]([N:9]([CH2:18][C:19]2[CH:38]=[CH:37][C:22]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 230830994-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine

Produkt 1

HCID 57541858Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoateAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine (313 mg), sodium hydride (60% oil, 50 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 1 hr. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (318 mg) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, acidified with 1N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The ethyl acetate layer was dried using Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by preparative HPLC (gradient cycle A) to give the title compound (150 mg, yield 28%) as a yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (gradient cycle A)

Quellen und Nachweise

ORD-Eintrag
ord-8f63154f9215437d896ab3bd116e09bb
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960369B2

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