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

HRID 1268313Notes

Reaction equation

HRID 1268313 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16](/[C:19](/[CH3:39])=[CH:20]/[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C@H:30]([O:36][CH2:37][CH3:38])[C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+]>>[F:1][C:2]([F:40])([F:41])[C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[CH:15][C:16](/[C:19](/[CH3:39])=[CH:20]/[CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][C@H:30]([O:36][CH2:37][CH3:38])[C:31]([OH:33])=[O:32])=[CH:25][CH:24]=3)=[CH:17][CH:18]=2)[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 20765811(E)-(S)-ethyl 3-{4-[3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate

Product 1

HCID 20765804(E)-(S)-3-{4-[3-(3',5'-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acidYield 90%

Procedure

The title compound was prepared from (E)-(S)-ethyl 3-{4-[3-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionate (Example 101) (625 mg, 1.08 mmol) and sodium hydroxide (1M, 4.3 ml, 4.3 mmol) by a procedure analogous to that described in example 51, yielding (E)-(S)-3-{4-[3-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid (535 mg, 90%) as a colourless gum.

Sources & evidence

ORD record
ord-65306070723c47f2a1151859a1be8f2a
Source dataset
uspto-grants-2003_04
Patent number
US06555577B1

Reaction notes

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