Triethylamine → Ethyl 2-[[3-[[[4-(2-pyridyloxy)phenyl]carbonylamino]methyl]-4-methoxyphenyl]methyl]butyrate

HRID 347670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347670
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].C(N(CC)CC)C.C(Cl)(=O)OCC.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=1>C(Cl)Cl>[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH:2][CH2:3][C:4]2[CH:5]=[C:6]([CH2:12][CH:13]([CH2:19][CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=[CH:8][C:9]=2[O:10][CH3:11])=[O:46])=[CH:43][CH:42]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22139981Ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochlorideHCID 222620524-(Pyridin-2-yloxy)benzoic acid

Produkt 1

HCID 21083633Ethyl 2-[[3-[[[4-(2-pyridyloxy)phenyl]carbonylamino]methyl]-4-methoxyphenyl]methyl]butyrateAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-[(3-aminomethyl-4-methoxyphenyl)-methyl]butyrate hydrochloride (302 mg, 1.00 mmol) [Japanese Patent Application No. 2000-158424] and triethylamine (390 μL, 2.80 mmol) in 10 mL of dehydrated methylene chloride was added ethyl chlorocarbonate (105 μL, 1.10 mmol) under cooling with ice and stirring, and the mixture was stirred for 20 minutes under cooling with ice. Next, 4-(2-pyridyloxy)benzoic acid (237 mg, 1.10 mmol) was added and the mixture was stirred for 1 hour under cooling with ice and for 5 hours at room temperature. Methylene chloride was added to the reaction mixture, which was washed with water, brine, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:2 v/v) to obtain 317 mg (68%) of the title compound as a colorless oil.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 20 minutes
  3. temperatureunder cooling with ice
  4. stirringthe mixture was stirred for 1 hour
  5. washwas washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-47b218c968d140058d444b0cec84a3e7
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176204B2

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