Sodium Hydroxide → (2S)-3-{4-[3-(4'-tert-Butyl-biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459236Notes

Reaction equation

C([O:3][C:4](=[O:20])[C@@H:5]([O:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16]Br)=[CH:9][CH:8]=1)C.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>>[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:16][CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:18][CH3:19])[C:4]([OH:3])=[O:20])=[CH:12][CH:11]=3)=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 88262[1,1'-Biphenyl]-4-ol, 4'-(1,1-dimethylethyl)-

HCID 58822859(2S)-3-[4-(3-Bromopropoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 10115645(2S)-3-{4-[3-(4'-tert-Butyl-biphenyl-4-yloxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

(2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 173, Step A was treated with 4′-tert-Butyl-biphenyl-4-ol from Step A under the Standard Procedure J. The compound thus obtained was allowed to react under Standard hydrolysis procedure C (NaOH) to give the title compound. MS(ES) for C29H34O5 [M+NH4]+: 480, [M+Na]+: 485.

Workup

customThe compound thus obtained

Sources & evidence

ORD record: ord-ec6d88d4d5e14ebfbaa499c7903c730e
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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