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

HRID 2427799노트

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HRID 2427799 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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-acc385733d37436783c11349caa0d5da
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968589B2

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