Sodium Hydroxide → 4-[3-[6-(3-Benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

HRID 418091Notes

Reaction equation

C([O:3][C:4](=[O:48])[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]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24]([C:32]3[CH:33]=[CH:34][C:35]4[S:39][CH:38]=[N:37][C:36]=4[CH:40]=3)[CH:23]=2)[C:10]=1[CH2:41][CH2:42][C:43]([O:45]CC)=[O:44])C.[OH-].[Na+]>>[S:39]1[C:35]2[CH:34]=[CH:33][C:32]([C:24]3[CH:23]=[C:22]([CH:27]=[C:26]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:25]=3)[O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]3[C:10]([CH2:41][CH2:42][C:43]([OH:45])=[O:44])=[C:9]([CH:14]=[CH:13][CH:12]=3)[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:48])=[O:3])=[CH:40][C:36]=2[N:37]=[CH:38]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 578630434-[3-[6-(3-Benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 442191594-[3-[6-(3-Benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acidYield 55.8%

Procedure

A similar procedure as described in Example 40, step 8 was used, starting from 4-[3-[6-(3-benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (100 mg, 0.14 mmol) and 1.0 N aqueous sodium hydroxide (1.44 mL) to afford 4-[3-[6-(3-benzothiazol-5-yl-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (50 mg, 54.4%) as an amorphous white solid: ES(+)-HRMS m/e calcd for C33H37NO8S2 (M+H)+ 640.2034, found 640.2030.

Sources & evidence

ORD record: ord-bf3a6d011ca54c0eb1b3df869da6533a
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

Loading…