Lithium Hydroxide → HCID 18443226, compound

HRID 459260Notes

Reaction equation

HRID 459260 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:34])[CH:6]([O:32][CH3:33])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[CH:10][C:9]=1[F:31]>C1COCC1.O>[C:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH:6]([O:32][CH3:33])[C:5]([OH:34])=[O:4])=[C:9]([F:31])[CH:10]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58823001HCID 58823001, compound

Product 1

HCID 18443226HCID 18443226, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1N aqueous lithium hydroxide solution (1.37 mL) was added to a solution of 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-fluoro-phenyl}-2-methoxy-propionic acid methyl ester (0.075 g, 0.17 mmol) in THF (2 mL) at room temperature. The reaction mixture was stirred overnight, diluted with water (10 mL), and extracted with diethyl ether (3×20 mL). The aqueous layer was acidified with 1N HCl to pH 1 and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-fluoro-phenyl}-2-methoxy-propionic acid as a white solid (60 mg, 83%). 1H-NMR (200 MHz, CDCl3): 7.56–7.29 (m, 7H), 7.18–7.09 (m, 1H), 6.98 (d, 2H, J=8.6), 6.66–6.60 (m, 2H), 4.17 (dt, 4H, J=8.9, 5.9), 4.03 (dd, 1H, J=6.7, 4.8), 3.40 (s, 3H), 3.23–3.14 (m, 1H), 2.97 (dd, 1H, J=14.0, 6.7), 2.26 (q, 2H, J=5.9)ppm.

Workup

  1. extractionextracted with diethyl ether (3×20 mL)
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4c392ae7bdc5461caab6eccaa809447c
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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