Triethylamine → Edonentan

HRID 1637708ノート

反応式

HRID 1637708 の反応式
[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]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 516919Sodium BisulfateHCID 15895426HCID 15895426、化合物

生成物 1

HCID 156690Edonentan

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-98c13c81902e422495c198a3d6e6f1b5
出典データセット
uspto-grants-2000_03
特許番号
US06043265

反応ノート

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