Trimethylsilyl iodide → {2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid

HRID 1642063Notes

Reaction equation

HRID 1642063 reaction equation
C([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:18])(=[O:8])[O:5]CC)C.C[Si](I)(C)C>C(Cl)Cl.C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:32]([O:31][C:28]1[CH:27]=[CH:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([C:17]([NH:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][P:4](=[O:3])([OH:8])[OH:5])=[O:18])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86638333{2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid diethylester

Product 1

HCID 24824095{2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

{2-[(4′-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid diethylester is dissolved in CH2Cl2 and and the mixture obtained is treated with trimethylsilyl iodide at 0°. The mixture obtained is stirred at 0° for several hours and diluted with toluene. From the mixture obtained solvent is evaporated. The evaporation residue obtained is dissolved in 1N NaOH solution, washed with EtOAc, HCl is added, precipitation occurs and the precipitate obtained is collected. {2-[(4′-Octyloxy-biphenyl-4-carbonyl)-amino]-benzyl}-phosphonic acid is obtained.

Workup

  1. customthe mixture obtained
  2. customThe mixture obtained
  3. customFrom the mixture obtained solvent
  4. customis evaporated
  5. customThe evaporation residue obtained
  6. washwashed with EtOAc, HCl
  7. additionis added
  8. customprecipitation
  9. customthe precipitate obtained
  10. customis collected

Sources & evidence

ORD record
ord-f5e0ed5eecc64310a2d55969935066ad
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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