Reaktion #79458

Reaktionsgleichung

DCC

3-(1-thyminyl)-propanoic acid

N-(N′-Boc-aminoethyl)glycine ethyl ester

Methylene chloride

→

title compound

Ausbeute 59.0%

N-(N′-Boc-aminoethyl)-N-[(1-thyminyl)propanoyl]glycine Ethyl Ester

Ausbeute 59.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITfollowed by 1 h at room temperature
2. 2
   SonstigeThe precipitated DCU was removed by filtration
3. 3
   Waschenwashed with methylene chloride (25 ml)
4. 4
   workup.ADDITIONa further amount of methylene chloride (50 ml) was added to the filtrate
5. 5
   ExtraktionThe organic phase was extracted with sodium hydrogen carbonate (1 volume saturated diluted with 1 volume water, 6×100 ml), potassium sulfate (1 volume saturated diluted with 4 volumes water, 3×100 ml), and saturated aqueous sodium chloride (1×100 ml)
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated to dryness, in vacuo
8. 8
   workup.STIRRINGstirred for 1 h
9. 9
   SonstigeThe precipitated DCU was removed by filtration
10. 10
    Waschenwashed with methylene chloride
11. 11
    SonstigeThe filtrate was evaporated to dryness, in vacuo
12. 12
    Sonstigethe residue purified by column chromatography on silica gel
13. 13
    Wascheneluting with a mixture of methanol and methylene chloride (gradient from 1 to 6% methanol in methylene chloride)

Vorschrift

N-(N′-Boc-aminoethyl)glycine ethyl ester (1.0 g, 0.0041 mol) was dissolved in DMF (12 ml). DhbtOH (0.73 g, 0.0045 mol) and 3-(1-thyminyl)-propanoic acid (0.89 g, 0.0045 mol) were added. Methylene chloride (12 ml) then was added and the mixture was cooled to 0° C. on an ice bath. After addition of DCC (1.01 g, 0.0049 mol), the mixture was stirred at 0° C. for 2 h, followed by 1 h at room temperature. The precipitated DCU was removed by filtration, washed with methylene chloride (25 ml), and a further amount of methylene chloride (50 ml) was added to the filtrate. The organic phase was extracted with sodium hydrogen carbonate (1 volume saturated diluted with 1 volume water, 6×100 ml), potassium sulfate (1 volume saturated diluted with 4 volumes water, 3×100 ml), and saturated aqueous sodium chloride (1×100 ml), dried over magnesium sulfate, and evaporated to dryness, in vacuo. The solid residue was suspended in methylene chloride (15 ml), and stirred for 1 h. The precipitated DCU was removed by filtration and washed with methylene chloride. The filtrate was evaporated to dryness, in vacuo, and the residue purified by column chromatography on silica gel, eluting with a mixture of methanol and methylene chloride (gradient from 1 to 6% methanol in methylene chloride). This afforded the title compound as a white solid (1.02 g, 59%). Anal. for C19H30N4O7, found (calc.) C, 53.15; (53.51); H, 6.90; (7.09); N, 12.76; (13.13). The compound showed satisfactory 1H and 13C-NMR spectra.

Quelle