Reaktion #77166

Reaktionsgleichung

3-benzyloxycarbonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

trifluoroacetic acid

→

white solid

3-(Benzyloxycarbonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter 30 minutes the reaction was concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in methylene chloride
3. 3
   workup.ADDITIONdiluted with hexane
4. 4
   FiltrationThe precipitated product was collected by filtration
5. 5
   Sonstigedried in vacuo

Vorschrift

To a solution of 3-benzyloxycarbonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (6.0 g, 17 mmol), as prepared in step 2 of Example 1, in methylene chloride (12 mL) was added trifluoroacetic acid (12 mL) and the reaction stirred at ambient temperature. After 30 minutes the reaction was concentrated in vacuo, dissolved in methylene chloride, and diluted with hexane. The precipitated product was collected by filtration and dried in vacuo giving a quantitative yield of white solid. 1H NMR (300 MHz, DMSO-d6) δ13.17 (br s, 1 H), 8.36 (s, 1H), 7.74 (d, 1H, J=7.5 Hz), 7.35 (m, 5H), 6.18 (d, 1H, J=7.7Hz), 5.15 (s, 2H), 4.77 (s, 2H), 2.25 (s, 3H).

Quelle