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

HRID 919031Notes

Reaction equation

HRID 919031 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, 2 H); 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-43b8783fb36640f1bc6eb1a31ca6a2cf
Source dataset
uspto-grants-2016_03
Patent number
US09272999B2

Reaction notes

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