Chloroform → HCID 118308766, compound

HRID 923472Notes

Reaction equation

HRID 923472 reaction equation
[CH3:1][C:2]1([CH3:16])[O:7][CH2:6][C:5]([N+:13]([O-])=O)([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][O:3]1.C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+].Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>C(O)(=O)C.[Zn]>[CH2:30]([O:29][C:27]([NH:13][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][O:7][C:2]([CH3:16])([CH3:1])[O:3][CH2:4]1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 118308716HCID 118308716, compound

Product 1

HCID 118308766HCID 118308766, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5.0 g of ethyl 2,2-dimethyl-5-nitro-1,3-dioxane-5-carboxylate in 50 ml of acetic acid was added 7 g of zinc powder in four divided portions at room temperature, followed by stirring at 45° C. for 4 hours. The insoluble materials of the reaction mixture were separated by filtration and washed with chloroform. The filtrate was concentrated under reduced pressure and neutralized by the addition of a saturated aqueous sodium hydrogen carbonate solution. To a mixture formed by adding 100 ml of chloroform thereto were added 2.7 g of sodium hydrogen carbonate and 3.7 ml of benzyl chloroformate at 0° C., followed by stirring at room temperature for 2 hours. The obtained organic layer was dried over anhydrous sodium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 6.6 g of ethyl 5-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-1,3-dioxane-5-carboxylate.

Workup

  1. customThe insoluble materials of the reaction mixture were separated by filtration
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionneutralized by the addition of a saturated aqueous sodium hydrogen carbonate solution
  5. customTo a mixture formed
  6. stirringby stirring at room temperature for 2 hours
  7. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55ce628d8a9144c48b2dd89de2444405
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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