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

HRID 628807Notes

Reaction equation

HRID 628807 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-de8b55a4e9cc4a6faed8be20d4239bc8
Source dataset
uspto-grants-2016_04
Patent number
US09315457B2

Reaction notes

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