Sodium Chloride → HCID 86755037, compound

HRID 849375Notes

Reaction equation

HRID 849375 reaction equation
[C:1]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[C@@H:2]([C@H:4]([C:6]([O:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[OH:5])[OH:3].[H-].[Na+].Br[C:31](Br)([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33].[Cl-].[Na+]>C(COC)OC.O>[O:5]1[C@@H:4]([C:6]([O:8][CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:7])[C@H:2]([C:1]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[O:3][C:31]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl esterHCID 53646624HCID 53646624, compound

Product 1

HCID 86755037HCID 86755037, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

3.92 g of tert-butyl diphenylmethyl L-tartarate was dissolved in 10 ml of dimethoxyethane, and 844 mg of 60% sodium hydride was added at 0° C. , followed by stirring at the same temperature for 45 minutes. Then, a solution of 3.37 g of diethyl dibromomalonate in 5 ml of dimethoxyethane, was added, followed by stirring under heating at 80° C. for 12 hours. The reaction solution was cooled to room temperature and then poured into water. The aqueous layer was saturated with sodium chloride and extracted with ethyl ether. The obtained organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1→5/1) to obtain 1.73 g (yield: 44%) of the above identified compound as white solid.

Workup

  1. stirringby stirring
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionextracted with ethyl ether
  4. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe drying agent was filtered off
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1→5/1)
  9. customto obtain 1.73 g (yield: 44%) of the

Sources & evidence

ORD record
ord-57b084dc21684e358c561fe9c07576e9
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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