Hydrochloric Acid → 4-{2-(2-Carboxy-ethyl)-3-[6-(3-methanesulfonyl-5-thiazol-4-yl-phenoxy)-hexyl]-phenoxy}-butyric Acid

HRID 418069Notes

Reaction equation

C([O:3][C:4](=[O:44])[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[N:29]=[CH:30][S:31][CH:32]=3)[CH:25]=[C:24]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:23]=2)[C:10]=1[CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])C.Cl>CCO.[OH-].[Na+]>[C:39]([CH2:38][CH2:37][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[N:29]=[CH:30][S:31][CH:32]=3)[CH:25]=[C:24]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:44])=[O:3])([OH:41])=[O:40]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-methanesulfonyl-5-thiazol-4-yl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (280 mg, 0.434 mmol) in EtOH (20 mL), 3N NaOH (1 mL) was added and heated at 70° C. for 2 h. The reaction was acidified with 3N HCl (1.1 mL). Concentration under reduced pressure gave an oil. Preparative HPLC provided title compound (119 mg, 46% yield). LC/MS indicated a purity of 92% as measured by UV 214 nM. HR-ES(+): calculated for C29H36NO8S2 (M+H)1+ 590.1877, found 590.1876.

Workup

concentrationConcentration under reduced pressure
customgave an oil

Sources & evidence

ORD record: ord-e987a87bb0d14e17abae07e987c652b5
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

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