Cesium carbonate → 3-{3-[3-(Biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459172Notes

Reaction equation

HRID 459172 reaction equation
C[O:2][C:3](=[O:15])[CH:4]([O:13][CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>CN(C=O)C>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([O:26][CH2:25][CH2:24][CH2:23][O:12][C:8]2[CH:7]=[C:6]([CH2:5][CH:4]([O:13][CH3:14])[C:3]([OH:2])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 152334631,1'-Biphenyl, 4-(3-bromopropoxy)-HCID 588228023-(3-Hydroxy-phenyl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 184431603-{3-[3-(Biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3-Hydroxyphenyl)-2-methoxy-propionic acid methyl ester (1 eq) from Step D, Cesium Carbonate (3 eq) and 4-(3-bromopropoxy)biphenyl (1 eq) in DMF and in a 10 mL tube was shaked in an orbital agitator over a weekend. The mixture was filtered through a hydrofobic syringer and evaporated in a speed-vac apparatus. Then diluted with NaOH 1N-Ethanol and stirred overnight. Then HCl 3N was added and the reaction mixture was concentrated to remove the ethanol in vacuo, reconstituted in dichloromethane and filtered through a hydrofobic syringe. The organic layer was evaporated to give the title compound. MS (ES) for C25H26O5 [M+NH4]+: 424.2, [M+Na]+: 429.2. 1H-NMR (CDCl3, 200.15 MHz): 7.57–7.17 (m, 9H), 6.98 (dd, 2H, J=6.7, 1.9), 6.84–6.81 (m, 3H), 4.19 (dd, 4H, J=14.0, 6.4), 4.03 (dd, 1H, J=7.3, 4.3), 3.40 (s, 3H), 3.13 (dd, 1H, J=14.2, 4.6), 2.98 (dd, 1H, J=14.0, 7.5), 2.28 (qui, 2H, J=5.9)ppm.

Workup

  1. waitin a 10 mL tube was shaked in an orbital agitator over a weekend
  2. filtrationThe mixture was filtered through a hydrofobic syringer
  3. customevaporated in a speed-vac apparatus
  4. additionThen diluted with NaOH 1N-Ethanol
  5. additionThen HCl 3N was added
  6. concentrationthe reaction mixture was concentrated
  7. customto remove the ethanol in vacuo
  8. filtrationfiltered through a hydrofobic syringe
  9. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-f6fb853bd48f49ec8acd2752baee7978
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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