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Thiophene → 2-(2-Amino-5-benzoyl-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

HRID 2088836
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2088836
[CH:1]1([N:7]([CH3:32])[S:8]([CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH:17][C:16]=2[N+:29]([O-])=O)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S1C=CC=C1>CO.[Pd]>[CH:1]1([N:7]([CH3:32])[S:8]([CH2:11][CH2:12][NH:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=[CH:17][C:16]=2[NH2:29])(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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Komponenten

5

Edukt 2

HCID 8030ThiopheneHCID 586251122-(5-Benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

Produkt 1

HCID 586251322-(2-Amino-5-benzoyl-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(5-benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide (0.009 mol) in methanol (150 mL) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of thiophene solution (1 mL). After uptake of H2 (3 equiv.), the catalyst was filtered off, and the filtrate was evaporated. The residue was purified by column chromatography over Biotage (eluent: 98:2 CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Aufarbeitung

  1. filtrationAfter uptake of H2 (3 equiv.), the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over Biotage (eluent: 98:2 CH2Cl2:CH3OH)
  4. customThe purest product fractions were collected
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7e714d7b01324e28960efd98c535a2d1
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436006B2

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