Triethylamine → HCID 18948415, compound

HRID 1768602Notes

Reaction equation

HRID 1768602 reaction equation
[CH2:1]([N:8]([CH2:10][CH:11]([OH:32])[CH2:12][CH:13]([CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[C:14]([O:16]C(C)(C)C)=[O:15])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O.O>[CH2:1]([N:8]([CH2:10][C:11](=[O:32])[CH2:12][CH:13]([CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[C:14]([OH:16])=[O:15])[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18948459HCID 18948459, compound

Product 1

HCID 18948415HCID 18948415, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

5.64 g of a sulfur trioxide/pyridine complex were added to a solution of 3.13 g (7.22 mmole) of t-butyl 5-(N-benzyl-N-methylamino)-4-hydroxy-2-(1-naphthylmethyl)pentanoate (prepared as described in Preparation 29) and 5 ml of triethylamine dissolved in 20 ml of dimethyl sulfoxide at room temperature, and the mixture was stirred for 2 hours. At the end of this time, the reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. 20 ml of a 4N solution of hydrogen chloride in dioxane were added to the residue, and the mixture was stirred for 2 hours; it was then concentrated by evaporation under reduced pressure. The residue was dissolved in water, and the resulting solution was neutralized by adding a 1N aqueous solution of sodium hydroxide. It was then concentrated by evaporation under reduced pressure. The residue was dissolved in methylene chloride and the resulting insoluble materials were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure to afford 1.94 g of the title compound as a colorless amorphous substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationafter which it was concentrated by evaporation under reduced pressure
  5. addition20 ml of a 4N solution of hydrogen chloride in dioxane were added to the residue
  6. stirringthe mixture was stirred for 2 hours
  7. concentrationit was then concentrated by evaporation under reduced pressure
  8. dissolutionThe residue was dissolved in water
  9. additionby adding a 1N aqueous solution of sodium hydroxide
  10. concentrationIt was then concentrated by evaporation under reduced pressure
  11. dissolutionThe residue was dissolved in methylene chloride
  12. customthe resulting insoluble materials were removed by filtration
  13. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-0f16fd970d5848c685fb64536b3a4123
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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