Diethyl Carbonate → HCID 15986126, compound

HRID 1900045Notes

Reaction equation

HRID 1900045 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19](=O)(OCC)[O:20]CC.C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH2:14][CH:15]([CH2:16][OH:17])[O:18][C:19]3=[O:20])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 7766Diethyl CarbonateHCID 10942334Sodium MethoxideHCID 23371846HCID 23371846, compound

Product 1

HCID 15986126HCID 15986126, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

2.4 g (9.62 mmol) of (RS)-3-(4-cyclohexyl-phenylamino)-propane-1,2-diol were dissolved in 50 ml of toluene, treated with 1.25 g (10.6 mmol) of diethyl carbonate and 0.4 ml of a 1 molar sodium methylate solution in methanol and stirred overnight at an oil bath temperature of 110°. The solvent was distilled off in a water-jet vacuum and the residue was treated with water and 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and the solvent was distilled off. 1.4 g of product in the form of yellowish crystals were obtained from ethyl acetate/hexane. A further 0.9 g of pure product was obtained from the mother liquor. M.p.: 167°-167.5°.

Workup

  1. distillationThe solvent was distilled off in a water-jet vacuum
  2. additionthe residue was treated with water and 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c6743dca8e084ccbb36dc87370ff48db
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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