Ethyl chloroacetate → HCID 136079629, compound

HRID 2068580Notes

Reaction equation

HRID 2068580 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16](=[O:23])[C:17]3[NH:18][CH:19]=[N:20][C:21]=3[N:22]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:15][C:16](=[O:23])[C:17]3[N:18]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:19]=[N:20][C:21]=3[N:22]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 136079632HCID 136079632, compound2×

Product 1

HCID 136079629HCID 136079629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6-oxo-6,7-dihydro-1H-purin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester, 3 (1 g), potassium carbonate and dimethylforamide was stirred at room temperature for 2 h, then the solution of ClCH2COOEt (0.38 g/5 mL dimethylforamide) was added drop-wise into the reaction mixture, After stirring for 15 h, the solution was then partitioned between ethyl acetate and water. The ethyl acetate solution was washed with water, then it was dried over sodium sulfate and filtered, evaporated under reduced pressure, and purification of the residue by use of column chromatography to give 4.

Workup

  1. stirringAfter stirring for 15 h
  2. customthe solution was then partitioned between ethyl acetate and water
  3. washThe ethyl acetate solution was washed with water
  4. dry with materialit was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure, and purification of the residue by use of column chromatography
  7. customto give 4

Sources & evidence

ORD record
ord-e6fd486a1f324dac948755ff423fdc3a
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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