Sodium Hydroxide → (E)-(S)-2-ethoxy-3-{4-[3-(4'-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionic acid

HRID 984426Notes

Reaction equation

HRID 984426 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18]/[CH:19]=[C:20](/[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)\[CH3:21])=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18]/[CH:19]=[C:20](/[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)=[CH:24][CH:23]=2)\[CH3:21])=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86589968(E)-(S)-Ethyl 2-Ethoxy-3-{4-[3-(4'-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionate

Product 1

HCID 69796786(E)-(S)-2-ethoxy-3-{4-[3-(4'-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionic acidYield 53%

Procedure

The title compound was prepared from (E)-(S)-ethyl 2-ethoxy-3-{4-[3-(4′-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionate (example 153) (463 mg, 1.0 mmol) and sodium hydroxide (1M, 1.5 ml, 1.5 mmol) by a procedure analogous to that described in example 51, yielding (E)-(S)-2-ethoxy-3-{4-[3-(4′-fluoro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-propionic acid (229 mg, 53%) as a colourless solid containing a trace of water.

Sources & evidence

ORD record
ord-c1ac9785f85445f4a538dd6568f44577
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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