Triethylamine → HCID 22104505, compound

HRID 1457319Notes

Reaction equation

HRID 1457319 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH:7]([CH2:14][C:15]([OH:17])=O)[CH2:6][CH2:5]2.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH:7]([CH2:14][C:15]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22104522HCID 22104522, compound

Product 1

HCID 22104505HCID 22104505, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalene-acetic acid (8.0 g), pyrrolidine (3.8 g) and benzotriazol-1-yloxy-tris(dimethyl-amino) phosphonium hexafluorophosphate (BOP Reagent,16.7 g) in dichloro-methane (80 ml) was added dropwise triethylamine (3.8 g) at 25° C., and the mixture was stirred for three hours. The mixture was concentrated under reduced pressure to remove the solvent, and to the residue were added water and toluene, and the insoluble materials were removed by filtration. The toluene layer was collected, washed successively with 1N aqueous sodium hydroxide solution, water and a saturated aqueous sodium chloride solution, an dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate=10:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (9.5 g) as an oily product.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove the solvent
  3. additionto the residue were added water and toluene
  4. customthe insoluble materials were removed by filtration
  5. customThe toluene layer was collected
  6. washwashed successively with 1N aqueous sodium hydroxide solution, water
  7. dry with materiala saturated aqueous sodium chloride solution, an dried over anhydrous sodium sulfate
  8. concentrationThe resultant was concentrated under reduced pressure
  9. customto remove the solvent
  10. customthe residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate=10:1)
  11. additionthe fractions containing the desired compound
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05e4b7a176d640db91d6eca7da407622
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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