Diethyl Carbonate → HCID 136247053, compound

HRID 1506854Notes

Reaction equation

HRID 1506854 reaction equation
[OH:1][NH:2][C:3]([CH:5]1[O:10][C:9]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:7]=2[O:6]1)=[NH:4].C[O-].[Na+].[C:31](=O)(OCC)[O:32]CC>C(O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:7]2[O:6][CH:5]([C:3]3[NH:4][C:31](=[O:32])[O:1][N:2]=3)[O:10][C:9]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)[C:8]=2[CH:23]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 10942334Sodium MethoxideHCID 178513410HCID 178513410, compound

Product 1

HCID 136247053HCID 136247053, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 500 mg N-hydroxy-6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carboxamidine in 3.7 ml ethanol was added 0.7 ml of a sodium methoxide solution (30% in methanol) and then 0.617 ml diethyl carbonate. The mixture was refluxed for 2 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was dissolved in 3.4 ml water and 1M aqueous HCl was added until pH7 was reached. The obtained precipitate was filtered, washed with water, dissolved in EtOAc and dried with MgSO4. Then the solvent was removed in vacuo and the crude product purified by preparative HPLC (C18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a solid. Yield: 257 mg.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 3.4 ml water
  4. addition1M aqueous HCl was added until pH7
  5. filtrationThe obtained precipitate was filtered
  6. washwashed with water
  7. dissolutiondissolved in EtOAc
  8. dry with materialdried with MgSO4
  9. customThen the solvent was removed in vacuo
  10. customthe crude product purified by preparative HPLC (
  11. washC18 reverse phase column, elution with water/MeCN gradient with 0.1% TFA)
  12. additionThe fractions containing the product
  13. customwere evaporated
  14. customto yield a solid

Sources & evidence

ORD record
ord-7d5dac41c0ed4f6a8ff8a7c968cb8d85
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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