Homoserine lactone hydrobromide → 1-(4-Methyl-benzyl)-3-(2-oxo-tetrahydro-furan-3-yl)-urea

HRID 1985214

Reaktionsgleichung

Reaktionsgleichung von HRID 1985214
Br.[NH2:2][CH:3]1[CH2:8][CH2:7][O:6][C:4]1=[O:5].[N:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[C:10]=[O:11].C(N(CC)C(C)C)(C)C>C1COCC1>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][NH:9][C:10]([NH:2][CH:3]2[CH2:8][CH2:7][O:6][C:4]2=[O:5])=[O:11])=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 73508Homoserine lactone hydrobromideHCID 81531DiisopropylethylamineHCID 27333881-(Isocyanatomethyl)-4-methylbenzene

Produkt 1

HCID 577189951-(4-Methyl-benzyl)-3-(2-oxo-tetrahydro-furan-3-yl)-ureaAusbeute 142,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 0° C. slurry of α-amino-γ-butyrolactone hydrobromide (25 g, 0.137 mol) in THF (200 mL) was combined with 1-isocyanatomethyl-4-methyl-benzene (20.6 g, 0.139 mol) and then treated dropwise with N,N-diisopropylethylamine (19.5 g, 0.151 mol). The reaction mixture was stirred for at room temperature for 2 h. The solvent was removed in vacuo to give 48.5 g crude 1-(4-methyl-benzyl)-3-(2-oxo-tetrahydro-furan-3-yl)-urea that was utilized directly in the next reaction without purification. MS (ES30 ) Calc'd for C13H17N2O3 (M+1) 249. Found m/z 249 (100%). 1H NMR.

Aufarbeitung

  1. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f56ded2aff7f4782a850d8dcb4a2681c
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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