Ethyl bromoacetate → HCID 58354052, compound

HRID 537010Notes

Reaction equation

HRID 537010 reaction equation
[C:1]([NH:9][C:10]1[C:15]([I:16])=[CH:14][NH:13][C:12](=[O:17])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C>[C:1]([NH:9][C:10]1[C:15]([I:16])=[CH:14][N:13]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12](=[O:17])[N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178522605HCID 178522605, compound

Product 1

HCID 58354052HCID 58354052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 8.3 g of N-benzoyl-5-iodocytosine dissolved in 60 ml DMF, was added at 0° C. 1.06 g of 55% NaH in mineral oil, and the solution was stirred at RT for 2 h. After 2.7 ml ethyl bromoacetate was added to the reaction mixture, the reaction solution was stirred for another 24 h at RT, which was followed by removal of the solvent under reduced pressure. The resulting residue was dissolved and the insoluble material was filtered off. The filtrate was washed two times with saturated aq ammonium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography (1:1 hexane/EA) to yield 6.5 g of compd 2 (compd b in Scheme 1) as a yellow solid. mp 154-5° C. 1H NMR (400 MHz; CDCl3) δ 13.31 (br s, 1H), 8.37 (d, J=7.2 Hz, 2H), 7.69 (s, 1H), 7.55 (t, J=7.4 Hz, 1H), 7.46 (t, J=7.6 Hz, 2H), 4.49 (s, 2H), 4.27 (q, J=7.2 Hz, 2H), 1.32 (t, J=7.2 Hz, 3H).

Workup

  1. additionwas added at 0° C
  2. customwhich was followed by removal of the solvent under reduced pressure
  3. dissolutionThe resulting residue was dissolved
  4. filtrationthe insoluble material was filtered off
  5. washThe filtrate was washed two times with saturated aq ammonium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (1:1 hexane/EA)
  9. customto yield 6.5 g of compd 2 (compd b in Scheme 1) as a yellow solid

Sources & evidence

ORD record
ord-c5bce7b74bdf45ba8cb8d52cee7b1c5f
Source dataset
uspto-grants-2014_10
Patent number
US08859766B2

Reaction notes

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