Tributylphosphine → HCID 89768067, compound

HRID 591576Notes

Reaction equation

HRID 591576 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][CH:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=3[Cl:23])=[CH:13][C:8]=2[O:7][CH2:6]1.[CH3:25][O:26][CH2:27][CH2:28][CH2:29]O.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1.C1COCC1.O>[Cl:23][C:17]1[CH:18]=[C:19]([O:22][CH2:29][CH2:28][CH2:27][O:26][CH3:25])[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][C:12]1[CH:11]=[CH:10][C:9]2[CH:5]([CH2:4][C:3]([OH:2])=[O:24])[CH2:6][O:7][C:8]=2[CH:13]=1

Participants

8

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 741163-Methoxy-1-propanolHCID 89768220HCID 89768220, compound

Product 1

HCID 89768067HCID 89768067, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of methyl(6-((2-chloro-4-hydroxybenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)acetate (34.9 mg) in toluene (0.25 mL) and THF (0.25 mL) were added a solution of 3-methoxy-1-propanol (13.5 mg) in toluene (0.5 mL) and a solution of tributylphosphine (40.5 mg) in toluene (0.5 mL). To the mixture was added ADDP (50.5 mg) and the mixture was stirred at room temperature overnight. To the mixture was added water (1.0 mL), and the mixture was extracted with EtOAc (2.0 mL). The organic layer was separated and concentrated. The residue was purified by preparative HPLC (C18, eluent: water/CH3CN (including 0.1% TFA)). After solvent evaporated, the residue was added 1.0 N NaOH (0.5 mL) and the mixture was stirred at 50° C. overnight. The mixture was added EtOAc (3.0 mL), and the organic layer was separated. The aqueous layer was acidified with 10% aqueous citric acid solution (0.5 mL), and extracted with EtOAc (3.0 mL). The organic layer was separated and concentrated. The residue was purified by preparative HPLC (C18, eluent: water/CH3CN (including 0.1% TFA)). The solvent was evaporated to give the title compound (13.1 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc (2.0 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC (C18, eluent: water/CH3CN (including 0.1% TFA))
  5. customAfter solvent evaporated
  6. additionthe residue was added 1.0 N NaOH (0.5 mL)
  7. stirringthe mixture was stirred at 50° C. overnight
  8. additionThe mixture was added EtOAc (3.0 mL)
  9. customthe organic layer was separated
  10. extractionextracted with EtOAc (3.0 mL)
  11. customThe organic layer was separated
  12. concentrationconcentrated
  13. customThe residue was purified by preparative HPLC (C18, eluent: water/CH3CN (including 0.1% TFA))
  14. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b9a9e2a1a2714ec5afe5899f01bb96f9
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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