Ethyl Acetate → 3-{3-Fluoro-4-[1-(2-methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl ester

HRID 1669341Notes

Reaction equation

HRID 1669341 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.[CH2:26]([O:28][C:29](=[O:43])[CH2:30][CH2:31][NH:32][C:33](=[O:42])[C:34]1[CH:39]=[CH:38][C:37](O)=[C:36]([F:41])[CH:35]=1)[CH3:27].C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:26]([O:28][C:29](=[O:43])[CH2:30][CH2:31][NH:32][C:33](=[O:42])[C:34]1[CH:39]=[CH:38][C:37]([O:15][CH:8]([C:6]2[CH:5]=[CH:4][C:3]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=3)=[C:2]([CH3:1])[CH:7]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[C:36]([F:41])[CH:35]=1)[CH3:27]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 597294013-(3-Fluoro-4-hydroxy-benzoylamino)-propionic acid ethyl esterHCID 597294401-(2-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptan-1-ol

Product 1

HCID 597294083-{3-Fluoro-4-[1-(2-methyl-4'-trifluoromethyl-biphenyl-4-yl)-heptyloxy]-benzoylamino}-propionic acid ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine 1-(2-methyl-4′-trifluoromethyl-biphenyl-4-yl)-heptan-1-ol (0.090 g, 0.25 mmol) and 3-(3-fluoro-4-hydroxy-benzoylamino)-propionic acid ethyl ester (0.050 g, 0.20 mmol) in toluene (1.0 mL). Add 1,1′(diazocarbonyl)dipiperidine (0.076 g, 0.3 mmol) followed by tributyl-phosphane (0.074 mL, 0.3 mmol) under inert atmosphere. Stir at room temperature for 16 hours. Dilute reaction with ethyl acetate filter and remove solvent under reduced pressure. Purify on silica gel chromatography (0-50% Ethyl acetate/hexanes gradient) to provide 0.105 g of title compound (90%).

Workup

  1. additionDilute
  2. filtrationfilter
  3. customremove solvent under reduced pressure
  4. customPurify on silica gel chromatography (0-50% Ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-2ca449309fdf41baad8672f9d624a2b7
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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