Triethylamine → HCID 86744889, compound

HRID 1086291Notes

Reaction equation

HRID 1086291 reaction equation
[CH:1]1([CH2:10][C:11]([N:13]2[CH2:26][CH2:25][CH2:24][C@H:14]2[C:15]([N:17]2[CH2:23][CH2:22][CH2:21][C@H:18]2[CH2:19][OH:20])=[O:16])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C>CS(C)=O>[CH:1]1([CH2:10][C:11]([N:13]2[CH2:26][CH2:25][CH2:24][C@H:14]2[C:15]([N:17]2[CH2:23][CH2:22][CH2:21][C@H:18]2[CH:19]=[O:20])=[O:16])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 70047990HCID 70047990, compound

Product 1

HCID 86744889HCID 86744889, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.53 g of 1-[1-(2-indenylacetyl)-L-prolyl]-L-prolinol prepared in Preparation Example 41 and 0.76 g of triethylamine were dissoved in 6 ml of dimethylsulfoxide. To the solution was added 1.19 g of sulfur trioxide-pyridine complex and the mixture was stirred for one hour at room temperature. The reaction mixture to which 10 ml of ice-water was added was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid, water, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel chromatography to produce 0.29 g of 1-[1-(2-indenylacetyl)-L-prolyl]-L-prolinal as a colorless oil (yield: 55%).

Workup

  1. additionTo the solution was added 1.19 g of sulfur trioxide-pyridine complex
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with diluted hydrochloric acid, water, and saturated sodium hydrogen carbonate in this order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-16616575bdf841c4a5b45e4b5b1bbf63
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

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