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

HRID 628807노트

반응식

HRID 628807 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-de8b55a4e9cc4a6faed8be20d4239bc8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315457B2

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