Hydrochloric Acid → 3-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acid ethyl ester

HRID 1993061Notes

Reaction equation

HRID 1993061 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=2[O:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=3[O:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:28][CH:29]=2)=[CH:9][CH:8]=1)[C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 578357253-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-propionic acid ethyl esterHCID 598551134'-Bromomethyl-2-butoxy-5-methyl-biphenyl

Product 1

HCID 591326263-[4-(2'-Butoxy-5'-methyl-biphenyl-4-ylmethoxy)-phenyl]-3-(4-fluorophenyl)-propionic acid ethyl esterYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 45.2 (48 mg, 0.166 mmol), 4′-Bromomethyl-2-butoxy-5-methyl-biphenyl (67 mg, 0.2 mmol) and cesium carbonate (81 mg, 0.25 mmol) in DMF (2 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water, acidified with dilute HCl, extracted into ethyl acetate, washed with water and dried over magnesium sulfate. The residue obtained after concentration was flash chromatographed on silica gel to obtain 45.3 (71 mg).

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe residue obtained
  5. concentrationafter concentration
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-b32c9ac20ca94e739c791ff6d9ac849d
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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