Sodium Hydroxide → 4-[2-(2-Carboxy-ethyl)-3-[6-(5-ethanesulfonyl-4'-chloro-biphenyl-3-yloxy)-hexyl]-phenoxy]-butyric acid

HRID 418109Notes

Reaction equation

C([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)[CH:25]=[C:26]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:27]=2)[C:10]=1[CH2:40][CH2:41][C:42]([O:44]CC)=[O:43])C.[OH-].[Na+]>>[C:42]([CH2:41][CH2:40][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=3)[CH:25]=[C:26]([S:28]([CH2:31][CH3:32])(=[O:29])=[O:30])[CH:27]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:47])=[O:3])([OH:44])=[O:43]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 578631024-[3-[6-(5-Ethanesulfonyl-4'-chloro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 578630794-[2-(2-Carboxy-ethyl)-3-[6-(5-ethanesulfonyl-4'-chloro-biphenyl-3-yloxy)-hexyl]-phenoxy]-butyric acidYield 99%

Procedure

A similar procedure as described in Example 40, step 8 was used, starting from 4-[3-[6-(5-ethanesulfonyl-4′-chloro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (116 mg, 0.17 mmol) and 1.0 N aqueous sodium hydroxide (1.7 mL) to afford 4-[2-(2-carboxy-ethyl)-3-[6-(5-ethanesulfonyl-4′-chloro-biphenyl-3-yloxy)-hexyl]-phenoxy]-butyric acid (106 mg, 99%) as an amorphous white solid: ES(+)-HRMS m/e calcd for C33H39ClO8S (M+Na)+ 653.1946, found 653.1948.

Sources & evidence

ORD record: ord-e4102fbd3aea4f16b534e96da156b19c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

Loading…