Triphenylphosphine → HCID 67341070, compound

HRID 1669273Notes

Reaction equation

HRID 1669273 reaction equation
[CH:1]1([CH2:7][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][O:27][C:28](=[O:41])[CH2:29][CH2:30][NH:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:26][O:27][C:28](=[O:41])[CH2:29][CH2:30][NH:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][C:36]([O:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 534159812-Cyclohexyl-1-[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]ethan-1-ol

Product 1

HCID 67341070HCID 67341070, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (±)-2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethanol (0.184 g, 0.527 mmol), 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (0.136 g, 0.608 mmol), and triphenylphosphine (0.208 g, 0.791 mmol) in toluene (8.0 mL) is treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.206 g, 0.817 mmol) and stirred overnight. The reaction mixture is filtered through Celite® diluted with EtOAc, washed with water (2×), brine (1×), dried over MgSO4, filtered, and conc. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 25% EtOAc to 100% EtOAc giving (±)-3-{4-[2-cyclohexyl-1-(4′-trifluoromethyl-biphenyl-4-yl)-ethoxy]-benzoylamino}-propionic acid methyl ester (0.091 g, 31%) as a white foam. MS (ES): 554.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture is filtered through Celite®
  2. additiondiluted with EtOAc
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. washeluted with hexanes using a gradient of 25% EtOAc to 100% EtOAc

Sources & evidence

ORD record
ord-5a40b1a5ac064cec83fda561578cbbf6
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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