4-Methylmorpholine → 3(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

HRID 1837871노트

반응식

HRID 1837871 반응식
Cl.[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O.F[P-](F)(F)(F)(F)F.[N:26]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34]C=2N=N1.[CH3:46][N:47]1CCOCC1.[C:53]([O:56][CH2:57][CH3:58])(=[O:55])[CH3:54]>CC#N>[CH2:57]([O:56][C:53](=[O:55])[CH2:54][C@@H:46]([C:33]1[CH:34]=[N:26][CH:30]=[CH:31][CH:32]=1)[NH:47][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH2:9][NH:10][C:11]=2[N:2]=1)[CH3:58]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 697750595-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid hydrochloride

생성물 1

HCID 544418963(S)-(Pyridin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-pentanoylamino)propionic acid ethyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-6 (50 mg, 0.1847 mmol), 1-7 (49 mg, 0.1847 mmol) (Rico et al., J. Org. Chem., 1993, 58, 7948), BOP (90 mg, 0.2032 mmol) and NMM (0.122 mL, 1.11 mmol) in CH3CN (2 mL) was stirred for 18 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 20% MeOH/ethyl acetate) to give 1-8 as a yellow oil.

후처리

  1. washwashed with sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 20% MeOH/ethyl acetate)

출처 및 근거

ORD 기록
ord-4a00a012af9d4e899a9273bf8579ed89
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784190B2

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