ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium hydride → 4-[2-Cyano-3-[[(3S)-hexahydro-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-azepin-3-yl]amino]-3-[(2-methyl-5-benzofuranyl)amino]-1-oxo-2-propenyl]benzoic acid methyl ester

HRID 1264627
ノート
印刷プレビュー

反応式

HRID 1264627 の反応式
[C:1]([CH2:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=[O:5])#[N:2].[H-].[Na+].[N:18]([C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([CH3:29])=[CH:26][C:25]=2[CH:30]=1)=[C:19]=S.[NH2:31][C@H:32]1[CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH2:39][C:40]([N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:41])[C:33]1=[O:47]>CN(C=O)C.C(OCC)(=O)C.[Hg](Cl)Cl>[CH3:13][O:12][C:10](=[O:11])[C:9]1[CH:14]=[CH:15][C:6]([C:4](=[O:5])[C:3]([C:1]#[N:2])=[C:19]([NH:31][C@H:32]2[CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH2:39][C:40](=[O:41])[N:42]3[CH2:43][CH2:44][CH2:45][CH2:46]3)[C:33]2=[O:47])[NH:18][C:21]2[CH:22]=[CH:23][C:24]3[O:28][C:27]([CH3:29])=[CH:26][C:25]=3[CH:30]=2)=[CH:7][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 736021Methyl 4-(cyanoacetyl)benzoateHCID 120478195-Isothiocyanato-2-methylbenzofuranHCID 12047820(S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine

生成物 1

HCID 700328734-[2-Cyano-3-[[(3S)-hexahydro-2-oxo-1-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-azepin-3-yl]amino]-3-[(2-methyl-5-benzofuranyl)amino]-1-oxo-2-propenyl]benzoic acid methyl ester
収率 49.3%

試薬・触媒・溶媒 3

HCID 24085Mercuric Chloride触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 4-(cyanoacetyl)benzoate (0.304 g, 1.50 mmol) in DMF (2 mL) was added sodium hydride (68.0 mg, 2.25 mmol). The reaction mixture was stirred at room temperature for 30 min. To the solution was then added 5-isothiocyanato-2-methylbenzofuran (0.284 g, 1.50 mmol). The reaction mixture was stirred at room temperature for 3 h at which time 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (0.358, 1.50 mmol) and mercury (II) chloride (0.407 g, 1.50 mmol) were added. The reaction mixture was stirred for another 30 min. The reaction mixture was passed through CELITE and diluted with 50 mL of ethyl acetate. The organic solution was washed 2×25 mL with brine and was concentrated in vacuo. The residue was purified by flash chromatography (silica, 4% methanol/ethyl acetate) to give the title compound as yellow solid (0.442 g, 49% yield): HPLC (method A) tR 4.1 min; MS (ESI, pos. ion spectrum) m/z 598 (M+H).

後処理

  1. additionwere added
  2. stirringThe reaction mixture was stirred for another 30 min
  3. washThe organic solution was washed 2×25 mL with brine
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica, 4% methanol/ethyl acetate)

出典と根拠

ORDレコード
ord-208b33a662b7400cbe1e6fdbf618205c
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06544981B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート