N-Boc-p-toluenesulfonamide → tert-Butyl methyl(tosyl)carbamate

HRID 393410

Reaktionsgleichung

Reaktionsgleichung von HRID 393410
[CH3:1]COC(/N=N/C(OCC)=O)=O.[C:13]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CO>[CH3:1][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)(=[O:23])=[O:22]

Komponenten

4

Edukt 2

HCID 688170N-Boc-p-toluenesulfonamideHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 22660067tert-Butyl methyl(tosyl)carbamateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The crude fluorous DEAD reagent 22 was then used in Mitsunobu reactions with N-Boc-p-toluenesulfonamide. Once again, the standard mode of addition gave complete conversion with MeOH and the product, N-methyl-N-boc-p-toluenesulfonamide was isolated in 85% yield after FSPE. However, the allyl alcohol gave only trace conversion of the starting material. The organic fraction after FSPE was mostly starting material. These results are summarized in Table 7.

Aufarbeitung

  1. additionOnce again, the standard mode of addition

Quellen und Nachweise

ORD-Eintrag
ord-41a99d97be5e482e8c5bb07a1cfdf604
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806357B1

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