N-BOC-ethylenediamine → (2-{3-[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-ethyl)-carbamic acid tert-butyl ester

HRID 25517

Reaktionsgleichung

Reaktionsgleichung von HRID 25517
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([N:16]=[C:17]=[S:18])[CH:15]=1.[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][NH2:31])=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(OCC)(=O)C>[C:21]([O:25][C:26](=[O:27])[NH:28][CH2:29][CH2:30][NH:31][C:17]([NH:16][C:14]1[CH:15]=[C:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:11]=[CH:12][C:13]=1[O:19][CH3:20])=[S:18])([CH3:24])([CH3:22])[CH3:23]

Komponenten

4

Edukt 2

HCID 187201N-BOC-ethylenediamineHCID 22568433[5-(1H-indol-2-yl)-2-methoxy-phenyl]-isothiocyanate2×

Produkt 1

HCID 10160475(2-{3-[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-thioureido}-ethyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The product from Example 26, Step A, [5-(1H-indol-2-yl)-2-methoxy-phenyl]-isothiocyanate, (0.272 g, 1.0 mmol) and mono-tert-butyloxycarbonyl ethylenediamine (0.156 g, 1.0 mmol) were heated briefly to 50° C. in ethyl acetate (20 mL). The reaction mixture was allowed to stand 1 hour at room temperature and was then concentrated. The residue was filtered through silica gel using hexanes/ethyl acetate as eluant The purest product-containing factions were combined, concentrated, and triturated with 3/1, hexanes/ethyl acetate, v/v, to give the product as an off-white solid (0.09 g), mp 159-160° C.

Aufarbeitung

  1. concentrationwas then concentrated
  2. filtrationThe residue was filtered through silica gel
  3. additionpurest product-containing factions
  4. concentrationconcentrated
  5. customtriturated with 3/1, hexanes/ethyl acetate, v/v

Quellen und Nachweise

ORD-Eintrag
ord-95de29cb25ad480fbdd559d44282b7e6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858739B2

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