Sodium Hydroxide → 3-[2-Chloro-4-[3-(4-phenoxy-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459213Notes

Reaction equation

HRID 459213 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([O:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[Cl:14])C.[O:18]([C:25]1[CH:35]=[CH:34][C:28]([O:29][CH2:30][CH2:31][CH2:32]O)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1.[OH-].[Na+]>>[Cl:14][C:8]1[CH:9]=[C:10]([O:13][CH2:32][CH2:31][CH2:30][O:29][C:28]2[CH:34]=[CH:35][C:25]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:26][CH:27]=2)[CH:11]=[CH:12][C:7]=1[CH2:6][CH:5]([O:15][CH3:16])[C:4]([OH:3])=[O:17]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 102435403-(4-Phenoxyphenoxy)-propan-1-olHCID 588230243-(2-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl esterHCID 178459888HCID 178459888, compound

Product 1

HCID 184435863-[2-Chloro-4-[3-(4-phenoxy-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

A mixture solution of 3-(2-Chloro-4-hydroxy-phenyl)-2-methoxy-propionic acid ethyl ester from Example 191, Step F and 3-(4-phenoxy-phenoxy)-propan-1-ol were allowed to react under the Standard Mitsounobu coupling conditions B (DIAD/toluene) to give the corresponding coupled product which by the Standard hydrolysis procedure C (NaOH) yield the title compound. MS (ES) for C25H25ClO6 [M+NH4]+: 474.

Workup

  1. customto give the

Sources & evidence

ORD record
ord-128da9f4f914476c98a94f2ba77c3854
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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