Diethyl Carbonate → HCID 54216092, compound

HRID 1900046Notes

Reaction equation

HRID 1900046 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH2:14][C@H: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>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH2:14][C@@H: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

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 10942334Sodium MethoxideHCID 54538643HCID 54538643, compound

Product 1

HCID 54216092HCID 54216092, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.40 g (5.6 mmol) of (S)-3-(4-cyclohexyl-phenylamino)-propane-1,2-diol in 50 ml of toluene was treated with 0.73 g (6.2 mmol) of diethyl carbonate and 0.5 ml of a 1 molar sodium methylate solution and stirred overnight at an oil bath temperature of 110°. After distilling off the solvent the residue was treated with water and 5 ml of 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over magnesium sulfate and the solvent was distilled off. 1.35 g of (S)-3-(4-cyclohexylphenyl)-5-hydroxymethyl-oxazolidin-2-one were obtained in the form of colorless crystals from ethyl acetate/hexane. M.p.: 166°-168°. [α]D =+51.25° (c=0.8/CH3OH).

Workup

  1. distillationAfter distilling off the solvent the residue
  2. additionwas treated with water and 5 ml of 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-96a0faa00d4443809ffdd5ed9e88f456
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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