Sodium Hydroxide → (E)-(S)-3-{4-[3-(3',5'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid

HRID 1268347Notes

Reaction equation

HRID 1268347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](/[C:15](/[CH3:33])=[CH:16]/[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:30][CH2:31][CH3:32])[C:27]([O-:29])=[O:28])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](/[C:15](/[CH3:33])=[CH:16]/[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:30][CH2:31][CH3:32])[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=3)=[CH:13][CH:14]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86758948(E)-(S)-3-{4-[3-(3',5'-Dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 69797174(E)-(S)-3-{4-[3-(3',5'-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acidYield 87%

Procedure

The title compound was prepared from (E)-(S)-ethyl 3-{4-[3-(3′,5′-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (example 125) (513 mg, 1.0 mmol) and sodium hydroxide (1M, 5.0 ml, 5.0 mmol) by a procedure analogous to that described in example 51, yielding (E)-(S)-3-{4-[3-(3′,5′-dichloro-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid (422 mg, 87%) as a colourless glass.

Sources & evidence

ORD record
ord-b6cc5b2a061944c784ccea7acf97cd06
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

Loading…