Fmoc isothiocyanate → N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thiourea

HRID 249733

Reaktionsgleichung

Reaktionsgleichung von HRID 249733
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH:16]1[C:28]2[CH:27]([CH2:29][O:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[C:12]([O:14][CH3:15])[N:13]=[C:3]([CH2:2][NH:1][C:34]([NH:33][C:31]([O:30][CH2:29][CH:27]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:28]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:32])=[S:35])[CH:4]=1)=[O:7])[CH3:10]

Komponenten

4

Edukt 2

HCID 4154759Fmoc isothiocyanateHCID 57791316Ethyl 2-aminomethyl-6-methoxyisonicotinate

Produkt 1

HCID 57791304N-(4-Ethoxycarbonyl-6-methoxypyridin-2-ylmethyl)-N'-(fluoren-9-ylmethyloxycarbonyl)thioureaAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

6.67 g (31.7 mmol) of ethyl 2-aminomethyl-6-methoxyisonicotinate (20d) were dissolved in 175 ml of toluene and treated at RT with 8.93 g (281.3 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After 15 minutes, the resulting precipitate was filtered off and dried at 50° C., 4.6 g of the title compound being isolated. The filtrate was concentrated, and the residue was taken up in DCM and washed three times with water. The organic phase was dried with MgSO4 and concentrated. The crude product thus obtained was chromatographed on silica gel (heptane/ethyl acetate 90:10→75:25), it being possible to isolate a further 8.1 g of the title compound.

Aufarbeitung

  1. filtrationthe resulting precipitate was filtered off
  2. customdried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-63dc31fe34c04da292513138d3624b13
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863269B2

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