Triethylamine → HCID 57080315, compound

HRID 486727Notes

Reaction equation

HRID 486727 reaction equation
[Cl:1][CH2:2][C@@H:3]([OH:15])[CH2:4][CH:5]([CH2:13]O)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C(Cl)Cl>[Cl:1][CH2:2][C@@H:3]([O:15][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:4][C:5](=[CH2:13])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57246443HCID 57246443, compound

Product 1

HCID 57080315HCID 57080315, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (4S)-5-chloro-4-hydroxy-2-hydroxymethylpentanoate (10.0 g) and triethylamine (12.7 g) in methylene chloride (100 ml), mesyl chloride (11.5 g) was added dropwise under ice-cooling and the mixture was stirred for 20 minutes. The mixture was concentrated in vacuo. Water was added to the residue and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was dissolved in benzene (130 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (7.0 g) was added to the solution. The mixture was stirred for 2 hours at room temperature. Water was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 11.1 g (89%) of tert-butyl (4S)-5-chloro-4-mesyloxy-2-methylenepentanoate.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo
  3. additionWater was added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe oily residue was dissolved in benzene (130 ml)
  9. addition1,8-diazabicyclo[5.4.0]undec-7-ene (7.0 g) was added to the solution
  10. stirringThe mixture was stirred for 2 hours at room temperature
  11. additionWater was added to the mixture
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with water and saturated sodium chloride solution
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated in vacuo
  16. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-59e95627597b4daeaf50bd3ed8e80158
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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