4-Hydroxybiphenyl → (2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid

HRID 459301

Reaction equation

HRID 459301 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.C([O:16][C:17](=[O:32])[C@@H:18]([O:30][CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28]Br)=[CH:22][CH:21]=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][C@H:18]([O:30][CH3:31])[C:17]([OH:32])=[O:16])=[CH:25][CH:24]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 71034-HydroxybiphenylHCID 10796Cesium carbonateHCID 58822865(2S)-3-[4-(2-bromo-ethoxy)-phenyl]2-methoxy-propionic acid ethyl ester

Product 1

HCID 10135109(2S)-3-{4-[2-(biphenyl-4-yloxy)-ethoxy]-phenyl}-2-methoxy-propionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of biphenyl-4-ol (0.39 mmol, 68 mg) in 10 ml of DMF in was treated with (2S)-3-[4-(2-bromo-ethoxy)-phenyl]-2-methoxy-propionic acid ethyl ester obtained in Step 2 (0.33 mmol, 100 mg) and cesium carbonate (0.66 mmol, 214 mg) in a round bottom flask. The reactants were filtered and was washed with DMF several times and the solvent was evaporated under vacuo. The residue was reconstituted in a mixture of ethanol (20 ml) and NaOH (1M) (8 ml), and then stirred at room temperature until TLC indicated the disappearance of starting material. Ethanol was removed under vacuum, and the aqueous solution was diluted with 20 ml of brine and washed with diethyl ether (3×15 mL). The aqueous phase was acidified with

Workup

  1. filtrationThe reactants were filtered
  2. washwas washed with DMF several times
  3. customthe solvent was evaporated under vacuo
  4. additionThe residue was reconstituted in a mixture of ethanol (20 ml) and NaOH (1M) (8 ml)
  5. customEthanol was removed under vacuum
  6. additionthe aqueous solution was diluted with 20 ml of brine
  7. washwashed with diethyl ether (3×15 mL)

Sources & evidence

ORD record
ord-ea7eb437cf5f4e2d980a993b393603bb
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Linked notes

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