Triphenylphosphine → HCID 18512374, compound

HRID 1370835Notes

Reaction equation

HRID 1370835 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:33]=[CH:32][C:23]([O:24][C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([O:57][CH2:58][CH3:59])(=[O:56])[CH2:54]O>C1COCC1.C(OCC)(=O)C>[CH2:58]([O:57][C:53](=[O:56])[CH2:54][O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:24][C:23]2[CH:32]=[CH:33][C:20]([CH2:19][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=3[CH3:18])=[CH:21][CH:22]=2)[CH:26]=1)[CH3:59]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 12184Ethyl GlycolateHCID 185122603-(4-{[Benzyl(2-methyl-3-nitrophenyl)amino]methyl}phenoxy)phenol

Product 1

HCID 18512374HCID 18512374, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 61F (1.29 g, 2.93 mmoles), triphenylphophine (1.54 g, 5.86 mmoles), and di-t-butylazodicarboxylate (1.01 g, 4.40 mmoles) in anhydrous THF (6 mL) were treated with ethyl glycolate (0.35 mL, 3.66 mmoles). The reaction was stirred overnight at room temperature. The mixture was diluted with ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a pre-packed Biotage silica gel column (hexanes to 10% ethyl acetate:hexanes) to provide the title compound.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a pre-packed Biotage silica gel column (hexanes to 10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-55dd2a13b0e14121995b7ebde523ba50
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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