Lawesson's reagent → 1,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamate

HRID 3141

Reaktionsgleichung

Reaktionsgleichung von HRID 3141
[C:1]([NH:8][C@H:9]([C:13]([NH2:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>C1COCC1>[C:1]([NH:8][C@H:9]([C:13](=[S:25])[NH2:15])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 11241393Boc-L-valine amide

Produkt 1

HCID 110207761,1-Dimethylethyl N-[(1S)-1-(aminothioxomethyl)-2-methylpropyl]carbamateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70%). NMR(CDCl3) δ 8.59 (1H, br s), 8.09 (1H, br s), 5.41 (1H, d (br)), 4.20 (1H, dd), 1.99 (1H, m), 1.39 (9H, s), 0.90 (6H, m).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue chromatographed (silica, 2.5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0a45a609ac2e45e08721ea94db9274b3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733882

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