Pyridine → {2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-phosphonic acid diethyl ester

HRID 1642066Notes

Reaction equation

HRID 1642066 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].N1C=CC=CC=1.[CH2:22]([O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43](Cl)=[O:44])=[CH:39][CH:38]=2)=[CH:33][CH:32]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C([O-])(O)=O.[Na+].CCOC(C)=O>CCOC(C)=O>[CH2:6]([O:5][P:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:43]([C:40]1[CH:39]=[CH:38][C:37]([C:34]2[CH:35]=[CH:36][C:31]([O:30][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:32][CH:33]=2)=[CH:42][CH:41]=1)=[O:44])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 12482984Diethyl (2-aminophenyl)phosphonateHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 24824666{2-[(4'-Octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At rt, to a solution of (2-Amino-phenyl)-phosphonic acid diethyl ester in EtOAc are added 10 equivaltents of pyridine followed by 1 equivalent of 4′-octyloxy-biphenyl-4-carbonylchloride (VAW132) and the mixture obtained is stirred for ca. 25 minutes. The mixture obtained is subjected to an aqueous work-up (NaHCO3/EtOAc), the organic phase obtained is dried, solvent is evaporated and the evaporation residue is subjected to column chromatography. {2-[(4′-Octyloxy-biphenyl-4-carbonyl)-amino]-phenyl}-phosphonic acid diethyl ester is obtained.

Workup

  1. customthe mixture obtained
  2. customThe mixture obtained
  3. customthe organic phase obtained
  4. customis dried
  5. customsolvent is evaporated

Sources & evidence

ORD record
ord-f43e521e39eb47a599501bdc2b52bd3d
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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