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

HRID 22894ノート

反応式

HRID 22894 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-de130ab3e91e4f1ea1f49e82f91d958a
出典データセット
uspto-grants-2005_02
特許番号
US06849639B2

反応ノート

読み込み中…