Diisopropylethylamine → Ethyl 3-{(1-(3-nitrophenyl)-5-oxopyrrolidin-3-yl) carbonylamino}-3-(3-pyridyl)propanoate

HRID 22894노트

반응식

HRID 22894 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([OH:18])=O)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:19][C:20]1([CH:26](C)[C:27]([O:29][CH2:30][CH3:31])=[O:28])C=CC=NC1.[CH:33]1[CH:38]=[N:37][C:36]2N(O)N=N[C:35]=2[CH:34]=1.CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([NH:19][CH:20]([C:35]3[CH:36]=[N:37][CH:38]=[CH:33][CH:34]=3)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:18])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27418301-(3-Nitrophenyl)-5-oxopyrrolidine-3-carboxylic acidHCID 69749277Ethyl 3-amino-3-pyridylpropanoate

생성물 1

HCID 22591756Ethyl 3-{(1-(3-nitrophenyl)-5-oxopyrrolidin-3-yl) carbonylamino}-3-(3-pyridyl)propanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-(3-nitrophenyl)-5-oxopyrrolidine-3-carboxylic acid (5 g, 0.02 mol), ethyl 3-amino-3-pyridylpropanoate (HCl salt) (0.03 mol) and HOAt (0.02 mol) in DMF (80 mL) at 0° C. was added i-Pr2NEt (0.03 mol), followed by 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.04 mol), in portions. The reaction mixture was then warmed up to room temperature and stirred overnight. The reaction solution was diluted with EtOAc (150 mL) and the organic phase was washed with saturated NaHCO3 and NaCl aqueous solution. The organic layer was dried over Na2SO4, concentrated in vacuo. The crude product was purified by flash column with 10% MeOH/EtOAc as eluent. Yellow solid was obtained. MS (ES+): 427.5 (M+H)+.

후처리

  1. washthe organic phase was washed with saturated NaHCO3 and NaCl aqueous solution
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column with 10% MeOH/EtOAc as eluent
  5. customYellow solid was obtained

출처 및 근거

ORD 기록
ord-de130ab3e91e4f1ea1f49e82f91d958a
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849639B2

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