Triphenylphosphine → HCID 86757788, compound

HRID 1699738Notes

Reaction equation

HRID 1699738 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:35])([F:34])[C:22]([NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=1)=[O:23].[CH3:36][O:37][C:38](=[O:55])[C:39]1[CH:44]=[C:43]([CH2:45]O)[CH:42]=[C:41]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([C:53]#[N:54])[CH:48]=2)[CH:40]=1.[Cl-].[NH4+]>CCOC(/N=N/C(OCC)=O)=O>[CH3:36][O:37][C:38](=[O:55])[C:39]1[CH:44]=[C:43]([CH2:45][O:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][CH2:25][NH:24][C:22](=[O:23])[C:21]([F:34])([F:35])[F:20])[CH:28]=2)[CH:42]=[C:41]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([C:53]#[N:54])[CH:48]=2)[CH:40]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 9881809HCID 9881809, compoundHCID 183695702,2,2-trifluoro-N-(2-(3-hydroxyphenyl)ethyl)ethanamide

Product 1

HCID 86757788HCID 86757788, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 5462977Diethyl azodicarboxylateSolvent

Procedure

110 mg of triphenylphosphine was dissolved in 5 ml of N-methylphosphine in the atmosphere of nitrogen, and 178 μl of DEAD was dropwisely dropped on the solution at 0° C. The obtained solution was mixed with 61 mg of (2,2,2-trifluoro-N-(2-(3-hydroxyphenyl)ethyl)ethanamide and 70 mg of 3-(3-cyanophenyl)-5-(hydroxymethyl)benzoic acid methyl ester, stirred at room temperature overnight and then poured on an aqueous solution of ammonium chloride to stop the reaction. The solution was extracted with ethyl acetate, and the obtained organic layer was dried. The solvent was distilled away, and the residue was purified by silica gel chromatography to obtain 79 mg (62.5%) of the title compound. Colorless solid.

Workup

  1. additionwas dropwisely dropped on the solution at 0° C
  2. customthe reaction
  3. extractionThe solution was extracted with ethyl acetate
  4. customthe obtained organic layer was dried
  5. distillationThe solvent was distilled away
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ee51d465add44f8091b2ac1b944bf328
Source dataset
uspto-grants-2002_02
Patent number
US06348478B1

Reaction notes

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