Dimethylformamide → Methyl n-{4-[2-(4-chlorophenyl)-1-propylpent-4-en-1-yl]benzoyl}-beta-alaninate

HRID 628807ノート

反応式

HRID 628807 の反応式
[CH3:1][N:2]([CH:4]=[O:5])C.[ClH:6].NC[CH2:9][C:10]([O:12][CH3:13])=[O:11].CCN([CH:20]([CH3:22])[CH3:21])C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1>CCOC(C)=O>[Cl:6][C:33]1[CH:38]=[CH:37][C:36]([CH:35]([CH2:22][CH:20]=[CH2:21])[CH:34]([C:33]2[CH:38]=[CH:37][C:36]([C:4]([NH:2][CH2:1][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:5])=[CH:35][CH:34]=2)[CH2:33][CH2:38][CH3:37])=[CH:35][CH:34]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2734767Methyl 3-aminopropanoate hydrochloride

生成物 1

HCID 67016514Methyl n-{4-[2-(4-chlorophenyl)-1-propylpent-4-en-1-yl]benzoyl}-beta-alaninate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A DMF solution (20 ml) containing INTERMEDIATE 1 (1.66 g, 4.84 mmol), methyl β-alaninate hydrochloride (1.01 g, 7.26 mmol), DIEA (4.3 ml, 24.2 mmol) and BOP (3.21 g, 7.26 mmol) was stirred at room temperature for 1.5 hours. The solution was diluted with EtOAc and washed with water, brine and dried over Na2SO4. The filtered solution was concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the title compound. 1H NMR for the major diastereomer (500 MHz, CDCl3): δ 7.72 (d, J=8.2 Hz, 2H); 7.28 (d, J=8.3 Hz, 2H); 7.22 (d, J=8.2 Hz); 7.07 (d, J=8.4 Hz, 2H); 6.85-6.81 (m, 1H); 5.41-5.31 (m, 1H); 4.77-4.66 (m, 2H); 3.75-3.70 (m, 2H); 3.73 (s, 3H); 2.81-2.72 (m, 2H); 2.67 (t, J=5.9 Hz, 2H); 2.10-2.05 (m, 2H); 1.40-1.29 (m, 2H); 0.98-0.85 (m, 2H); 0.66 (t, J=7.3 Hz, 3H). LC1 4.03 min. (M+H)=428

後処理

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe filtered solution was concentrated
  4. customthe residue purified by silica gel chromatography

出典と根拠

ORDレコード
ord-de8b55a4e9cc4a6faed8be20d4239bc8
出典データセット
uspto-grants-2016_04
特許番号
US09315457B2

反応ノート

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