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

HRID 2246887Notes

Reaction equation

HRID 2246887 reaction equation
CC(C1NC(=O)C(CCSC)NC(=O)C(NC(C(NC(C(NC(C(NC(C(N)CC(O)=O)=O)C(O)C)=O)CCSC)=O)CCCNC(N)=N)=O)CSSCC(C(N[CH:90]([C:101](NC(C(NC(C(O)=O)C(C)C)=O)CCC(O)=O)=O)[CH2:91][C:92]2[C:100]3[C:95](=[CH:96][CH:97]=[CH:98][CH:99]=3)N[CH:93]=2)=O)NC(=O)C2N(CCC2)C(=O)C(CCCNC(N)=N)NC(=O)C(CC2C=CC(O)=CC=2)NC(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC1=O)C.[ClH:145].[NH2:146][CH2:147][CH2:148][C:149]([O:151][CH3:152])=[O:150].CCN(C(C)C)[CH:156]([CH3:158])[CH3:157].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:173]2[CH:174]=[CH:175][CH:176]=[CH:177][C:172]=2N=N1.CCO[C:192](C)=[O:193]>CN(C=O)C>[Cl:145][C:97]1[CH:98]=[CH:99][C:100]([CH:92]([CH2:91][CH:90]=[CH2:101])[CH:93]([C:176]2[CH:177]=[CH:172][C:173]([C:192]([NH:146][CH2:147][CH2:148][C:149]([O:151][CH3:152])=[O:150])=[O:193])=[CH:174][CH:175]=2)[CH2:157][CH2:156][CH3:158])=[CH:95][CH:96]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 16167454Melanin-concentrating hormone

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-29de21ac1f9147caba439d248ffbf585
Source dataset
uspto-grants-2010_03
Patent number
US07687534B2

Reaction notes

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