Triethylamine → Edonentan

HRID 1637708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637708
[CH3:1][C:2]1[C:3]([NH:8][S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29][NH:30][CH3:31])=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].C(N(CC)CC)C.[C:39]([CH2:43][C:44](Cl)=[O:45])([CH3:42])([CH3:41])[CH3:40].OS([O-])(=O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:3]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[O:25][CH:26]=[CH:27][N:28]=3)=[CH:20][C:19]=2[CH2:29][N:30]([CH3:31])[C:44](=[O:45])[CH2:43][C:39]([CH3:42])([CH3:41])[CH3:40])(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 516919Sodium BisulfateHCID 15895426HCID 15895426, Verbindung

Produkt 1

HCID 156690Edonentan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the title product of Step F in 300 ml of CH2Cl2 at 0° C., triethylamine (6.17 g, 60.96 mmol) was added and stirred for 5 minutes. To the mixture, t-butylacetyl chloride (3.98 g, 29.57 mmol) was added dropwise over 10 minutes. The reaction mixture was stirred at 0° C. for 10 minutes and at room temperature for 1 hr. 100 ml 10% aqueous NaHSO4 was added. The aqueous layer was extracted with 100 ml CH2Cl2. The combined organic extracts were washed with 100 ml H2O, 50 ml brine, dried and concentrated. The residue was chromatographed on silica gel using 60:40:1 hexane/EtOAc/AcOH to provide the title product of this Example (13.10 g, 80% for two steps) as a white solid. melting point=120-128° C. (amorphous).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 0° C. for 10 minutes and at room temperature for 1 hr
  2. extractionThe aqueous layer was extracted with 100 ml CH2Cl2
  3. washThe combined organic extracts were washed with 100 ml H2O, 50 ml brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 60:40:1 hexane/EtOAc/AcOH

Quellen und Nachweise

ORD-Eintrag
ord-98c13c81902e422495c198a3d6e6f1b5
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043265

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