Dibenzylphosphite → HCID 178527045, compound

HRID 1993122Notes

Reaction equation

HRID 1993122 reaction equation
[CH2:1]([O:8][P:9]([O-:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC1C=CC=C(CC([O-])=O)C=1CC([O-])=O>CC#N>[CH2:11]([O:10][PH:9](=[O:18])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21904359DibenzylphosphiteHCID 219456882-[2-(Carboxylatomethyl)-3-iodophenyl]acetate

Product 1

HCID 178527045HCID 178527045, compoundYield 381.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 13 (0.80 g, 0.93 mmol) and 1H-tetrazole (98 mg, 1.39 mmol) in CH2Cl2 (15 mL) was treated with dibenzyldiisopropylphosphoramidite (0.43 mL, 1.39 mmol) and stirred at room temperature overnight. The product was partitioned between CH2Cl2 and H2O, dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography to give the intermediate dibenzylphosphite (0.68 g, 67%). To a solution of the dibenzylphosphite (0.39 g, 0.35 mmol) in CH3CN (5 mL) was added iodobenzenediacetate (0.17 g, 0.53 mmol). The reaction mixture was stirred at room temperature for 2 h and concentrated. The residue was partitioned between EtOAc and NaHCO3. The organic layer was washed with H2O, dried with Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography on silica gel (3% 2-propanol/CH2Cl2) to give the dibenzylphosphonate (0.35 g, 88%) as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between EtOAc and NaHCO3
  3. washThe organic layer was washed with H2O
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography on silica gel (3% 2-propanol/CH2Cl2)

Sources & evidence

ORD record
ord-edb92aaf089140a19f712e8ce3f58b78
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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