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

HRID 1268344Notes

Reaction equation

HRID 1268344 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](/[C:15](/[CH3:35])=[CH:16]/[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](/[C:15](/[CH3:35])=[CH:16]/[CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[CH:21][CH:20]=3)=[CH:13][CH:14]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86589963(E)-(S)-ethyl 3-{4-[3-(3',5'-dibromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 69796302(E)-(S)-3-{4-[3-(3',5'-dibromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acidYield 87.1%

Procedure

The title compound was prepared from (E)-(S)-ethyl 3-{4-[3-(3′,5′-dibromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (example 123) (110 mg, 0.18 mmol) and sodium hydroxide (1M, 1.0 ml, 1.0 mmol) by a procedure analogous to that described in example 51, yielding (E)-(S)-3-{4-[3-(3′,5′-dibromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid (90 mg, 86%) as a colourless gum.

Sources & evidence

ORD record
ord-60107b2edfe343349e29cba9e86867da
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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