Hydrochloric Acid → HCID 18443527, compound

HRID 459298Notes

Reaction equation

HRID 459298 reaction equation
[CH2:1](I)[CH3:2].[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([OH:26])[C:23]([OH:25])=[O:24])=[C:17]([Cl:27])[CH:16]=2)=[CH:6][CH:5]=1.Cl>CN(C=O)C>[C:4]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:26][CH2:1][CH3:2])[C:23]([OH:25])=[O:24])=[C:17]([Cl:27])[CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 18443632HCID 18443632, compound

Product 1

HCID 18443527HCID 18443527, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl iodide (0.6 mmol, 0.05 mL) was added to a solution of 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-chloro-phenyl}-2-hydroxy-propionic acid (Step A) and Ag2O (0.09 mmol, 21 mg) in DMF (0.5 mL). The mixture was heated at 50° C. for 24 hours. The mixture was warmed to room temperature, and 1N HCl was added until pH 3. The aqueous phase was extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated. The crude was purified by chromatography on silica gel (CH2Cl2) to afford the title compound. 1H-NMR (CDCl3, 300.15 MHz): δ 7.56–7.51 (m, 4H), 7.44–7.39 (m, 2H), 7.30 (t, 1H, J=7.3), 7.20 (d, 1H, J=8.5), 6.99 (d, 2H, J=8.7), 6.95 (d, 1H, J=2.4), 6.77 (dd, 1H, J=8.5, 2.4), 4.21–4.13 (m, 5H), 3.64–3.54 (m, 1H), 3.44–3.34 (m, 1H), 3.29 (dd, 1H, J=14.1, 4.2), 3.01 (dd, 1H, J=14.1, 8.7), 2.28 (qn, 2H, J=6.0), 1.12 (t, 3H, J=6.9).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-1559fed737ea4d9b910be4d16d88ef96
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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