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

HRID 984377Notes

Reaction equation

HRID 984377 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13](/[C:16](/[CH3:36])=[CH:17]/[CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][C@H:27]([O:33][CH2:34][CH3:35])[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+]>>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13](/[C:16](/[CH3:36])=[CH:17]/[CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][C@H:27]([O:33][CH2:34][CH3:35])[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86589953(E)-(S)-Ethyl 3-{4-[3-(3'-Acetyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 69800550(E)-(S)-3-{4-[3-(3'-acetyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acidYield 25%

Procedure

The title compound was prepared from (E)-(S)-ethyl 3-{4-[3-(3′-acetyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (Example 105) (140 mg, 0.288 mmol) and sodium hydroxide (1M, 0.58 ml, 0.58 mmol) by a procedure analogous to that described in example 51, yielding (E)-(S)-3-{4-[3-(3′-acetyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid (33 mg, 25%) as a yellow coloured solid.

Sources & evidence

ORD record
ord-15e4d848ba724124936df054557c4853
Source dataset
uspto-grants-2005_03
Patent number
US06867218B2

Reaction notes

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