Diisopropylethylamine → 4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-oxo-butyramide

HRID 1818658ノート

反応式

HRID 1818658 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:14][CH2:15][NH2:16])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]#[CH:13].C(N(CC)C(C)C)(C)C.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:40])[CH2:34][CH:35]([OH:39])[C:36](O)=[O:37])=[CH:29][CH:28]=1.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)C=O>[Cl:26][C:27]1[CH:28]=[CH:29][C:30]([C:33](=[O:40])[CH2:34][CH:35]([OH:39])[C:36]([NH:16][CH2:15][CH2:14][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]#[CH:13])=[C:4]([O:3][CH3:2])[CH:5]=2)=[O:37])=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 30672534-(4-Chlorophenyl)-2-hydroxy-4-oxobutanoic acidHCID 857743992-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine hydrochloride

生成物 1

HCID 578850664-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-oxo-butyramide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-(3-Methoxy-4-prop-2-ynyloxy-phenyl)-ethylamine hydrochloride (5.4 g, 22 mmol) and N,N-diisopropylethylamine (11 g, 83 mmol) are dissolved in 70 ml of N,N-dimethylformamide. To this solution 4-(4-chloro-phenyl)-2-hydroxy-4-oxo-butyric acid (4.8 g, 21 mmol) and (benzotriazol-1-yloxy)-tris-(dimethylamino)-phosphonium hexafluorophosphate (10 g, 23 mmol) are added successively. The reaction mixture is stirred for 16 hours at room temperature, subsequently poured on ice-water and extracted several times with ethyl acetate. The combined organic layer is washed with brine, dried over sodium sulfate and evaporated in vacuum. The remaining oil is purified by chromatography on silicagel (ethyl acetate/hexane 6:4) to give 4-(4-chloro-phenyl)-2-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-4-oxo-butyramide (Compound E1.10).

後処理

  1. additionsubsequently poured on ice-water
  2. extractionextracted several times with ethyl acetate
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuum
  6. customThe remaining oil is purified by chromatography on silicagel (ethyl acetate/hexane 6:4)

出典と根拠

ORDレコード
ord-bfdbfcadb90a42bcad5e0b5236cc9b7d
出典データセット
uspto-grants-2009_10
特許番号
US07601674B2

反応ノート

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