Triethylamine → HCID 178501048、化合物

HRID 1797007ノート

反応式

HRID 1797007 の反応式
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)=O.[CH3:16][O:17][C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26](O)=O)[CH2:22][CH2:21]1)=[O:19].C([N:31](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O.CC(O)=O>[CH3:16][O:17][C:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26]2[NH:2][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=3)[N:31]=2)[CH2:22][CH2:21]1)=[O:19]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 133658852-Amino-1-(3-(trifluoromethyl)phenyl)ethan-1-one hydrochlorideHCID 178501163HCID 178501163、化合物

生成物 1

HCID 178501048HCID 178501048、化合物

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

The solution of 2-amino-1-(3-trifluoromethyl-phenyl)-ethanone hydrochloride (50.2 mmol), trans-cyclohexane-1,4-dicarboxylic acid monomethyl ester (50.2 mmol), triethylamine (100.4 mmol) and BOP (50.2 mmol) in DMF (100 mL) was stirred overnight at room temperature. The mixture was diluted with water, extracted with EtOAc, washed with saturated NaHCO3 and brine, dried over Na2SO4, and concentrated under vacuum. The residue was triturated with ether and the precipitate was collected. The precipitate was mixed with NH4OAc (930 mmol) and 200 ml of AcOH and refluxed overnight. The excess AcOH was removed and purification by flash chromatography (95:5 CH2Cl2/MeOH) gave trans-4-[4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexyl-carboxylic acid methyl ester.

後処理

  1. extractionextracted with EtOAc
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with ether
  6. customthe precipitate was collected
  7. temperaturerefluxed overnight
  8. customThe excess AcOH was removed
  9. custompurification by flash chromatography (95:5 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-84b3799ec96d42c7be06cf1fee7b4be8
出典データセット
uspto-grants-2006_04
特許番号
US07034034B2

反応ノート

読み込み中…