Sodium Hydroxide → 4-{2-(2-Carboxy-ethyl)-3-[6-(3-pyrimidin-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy}-butyric acid

HRID 420375Notes

Reaction equation

C([O:3][C:4](=[O:46])[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:27]=[C:26]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:25]=[C:24]([C:33]3[CH:34]=[N:35][CH:36]=[N:37][CH:38]=3)[CH:23]=2)[C:10]=1[CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])C.[OH-].[Na+]>>[C:41]([CH2:40][CH2:39][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)[CH:25]=[C:24]([C:33]3[CH:38]=[N:37][CH:36]=[N:35][CH:34]=3)[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:46])=[O:3])([OH:43])=[O:42]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 575864554-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-pyrimidin-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester

Product 1

HCID 251921754-{2-(2-Carboxy-ethyl)-3-[6-(3-pyrimidin-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy}-butyric acidYield 93%

Procedure

A similar procedure as described in Example 12, step 9 was used, starting from 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-pyrimidin-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (137 mg, 0.21 mmol) and 1.0 N aqueous NaOH (6 mL) to give 4-{2-(2-carboxy-ethyl)-3-[6-(3-pyrimidin-5-yl-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy}-butyric acid (115 mg, 93%) as an amorphous light yellow solid: ES(+)-HRMS m/e calculated for C33H36N2O6S (M+H)+ 589.2367, found 589.2366.

Sources & evidence

ORD record: ord-99ee0f4ff3da4b5abea790bbd06aebbc
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093385B2

Reaction notes

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