Triphenylphosphine → 3-[4-(2-Pyridinylamino)butoxy]phenyl-3-methylbutanoic acid

HRID 2085057Notes

Reaction equation

HRID 2085057 reaction equation
N1C=CC=CC=1N[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]([CH:22]([CH3:24])[CH3:23])[C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.OCCC[CH2:48][NH:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][N+:51]=1[O-].N(C(OCC)=O)=NC(OCC)=O>CN(C=O)C>[N:51]1[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=1[NH:49][CH2:48][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]([CH:22]([CH3:23])[CH3:24])[C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 226027013-[3-(2-Pyridinylamino)propoxy]phenyl-3-methylbutanoic acidHCID 178526250HCID 178526250, compound

Product 1

HCID 226026993-[4-(2-Pyridinylamino)butoxy]phenyl-3-methylbutanoic acidYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of the product from Example 5, Step 3 (720 mg, 3.24 mmol) in DMF (9 mL) was added triphenylphosphine (850 mg, 3.24 mmol). The reaction solution was kept at ambient temperature for 1 hour and a solution of 2-(4-hydroxybutylamino)pyridine N-oxide (590 mg, 3.24 mmol) and diethyl azodicarboxylate (0.51 mL, 3.24 mmol) in DMF (5 mL) was added. The reaction solution was kept at room temperature for 18 hours and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The aqueous solution was back extracted with ethyl acetate. The combined organic solution was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (98:1:1 CH2Cl2:MeOH:NH4OH) to give the desired product, (560 mg, 45% yield).

Workup

  1. waitThe reaction solution was kept at room temperature for 18 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous solution was back extracted with ethyl acetate
  6. washThe combined organic solution was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography (98:1:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-079ac4cdb2aa49b08a17a38bc4e72864
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

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