Dimethylformamide → [4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester

HRID 349616Notes

Reaction equation

HRID 349616 reaction equation
[N:1]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C(N1C=CN=C1)(N1[CH:19]=[CH:18]N=C1)=O.[CH2:25]([OH:35])[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1.CN([CH:39]=[O:40])C>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][N:1]1[CH:8]=[CH:7][C:5]([NH:6][C:39]([O:35][CH2:25][C:26]2[CH:34]=[CH:33][C:32]3[O:31][CH2:30][O:29][C:28]=3[CH:27]=2)=[O:40])=[N:4][C:2]1=[O:3])[CH3:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10322Piperonyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 21868458HCID 21868458, compound

Product 1

HCID 68524231[4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl esterYield 96%

Conditions

Temperature
100 °C

Procedure

The reaction mixture of (cytosin-1-yl)-acetic acid (3.94 g, 20 mmol) and 1,1′-carbonyldiimidazole (4.86 g, 30 mmol) in DMF was stirred for 25 min. at 100° C. Then, piperonyl alcohol (6.08 g, 40 mmol) was added to the reaction mixture. The resulting reaction mixture was allowed to cool to room temperature for 2 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with water (100 mL×2), dried over MgSO4, and filtered. The filtrate was concentrated in vacuo and treated with ethyl ether to afford white solid. The solid was filtered off and dried in vacuo to give the desired product (7.20 g, 96%). 1H-NMR (500 MHz; DMSO-d6) δ 10.77 (s, 1H), 8.04 (d, 1H), 7.04 (d, 1H), 7.00 (s, 1H), 6.92 (s, 2H), 6.02 (s, 2H), 5.09 (s, 2H), 4.61 (s, 2H), 4.15 (q, 2H), 1.19 (t, 3H).

Workup

  1. customThe resulting reaction mixture
  2. temperatureto cool to room temperature for 2 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe solution was washed with water (100 mL×2)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. additiontreated with ethyl ether
  10. customto afford white solid
  11. filtrationThe solid was filtered off
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c356229837c24ff8909ba5dc81a93bfd
Source dataset
uspto-grants-2007_02
Patent number
US07179896B2

Reaction notes

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