Triethylamine → 2-[(R)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

HRID 842280

Reaktionsgleichung

Reaktionsgleichung von HRID 842280
[NH2:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)[CH2:3][OH:4].C(N(CC)CC)C.[CH3:28][O:29][C@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:28][O:29][C@@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31]([NH:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=1)[CH2:3][OH:4])=[O:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3080792(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chlorideHCID 100642062-Amino-4-(4-octylphenyl)butan-1-ol

Produkt 1

HCID 701464362-[(R)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Amino-4-(4-octylphenyl)butanol (10 mg), N,N-dimethyl-p-aminopyridine (17.5 mg), anhydrous triethylamine (11.4 μl) and anhydrous methylene chloride (1 ml) were mixed and the mixture was stirred under a nitrogen atmosphere at room temperature. Thereto was added (R)-α-methoxy-α-trifluoromethylphenylacetyl chloride (16.8 μl) and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by thin layer chromatography (eluent; chloroform:methanol=9:1) to give the two diastereomer mixtures. Moreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute) to give the subject oily substance (9.8 mg) of 67.8 minutes at retention time and the subject oily substance (9.6 mg) of 71.6 minutes at retention time.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by thin layer chromatography (eluent; chloroform:methanol=9:1)
  5. customto give the two diastereomer mixtures
  6. customMoreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute)
  7. customto give the subject oily substance (9.8 mg) of 67.8 minutes at retention time
  8. customthe subject oily substance (9.6 mg) of 71.6 minutes

Quellen und Nachweise

ORD-Eintrag
ord-87dd6862c20c4ff9ad6582dd8128191d
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372800B1

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