Sodium Hydroxide → 4-[3-[6-(3-Acetyl-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

HRID 417033Notes

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 594968224-[3-[6-(3-Acetyl-5-benzo[1,3]-dioxol-5-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 469290794-[3-[6-(3-Acetyl-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acidYield 92%

Procedure

A similar procedure as described in Example 43, step 5 was used, starting from 4-[3-[6-(3-acetyl-5-benzo[1,3]-dioxol-5-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (230 mg, 0.36 mmol) and 1.0 N aqueous sodium hydroxide (8 mL) to afford 4-[3-[6-(3-acetyl-5-benzo[1,3]dioxol-5-yl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (192 mg, 92%) as a white solid: ES(+)-HRMS m/e calcd for C34H38O9 (M+Na)+ 613.2408. found 613.2407.

Sources & evidence

ORD record: ord-dffa31810a124171bac610481e14f008
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

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