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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1264627
[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
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Komponenten

8

Edukt 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

Produkt 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
Ausbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24085Mercuric ChlorideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-208b33a662b7400cbe1e6fdbf618205c
Quelldatensatz
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06544981B2

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