Sodium Hydroxide → 4-{2-(2-Carboxy-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric Acid

HRID 418066Notes

Reaction equation

C([O:3][C:4](=[O:40])[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]([I:32])[CH:23]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37]CC)=[O:36])C.[OH-].[Na+]>C(O)C.CCOC(C)=O>[C:35]([CH2:34][CH2:33][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]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24]([I:32])[CH:23]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:40])=[O:3])([OH:37])=[O:36]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-methanesulfonyl-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (0.9 g, 1.31 mmol) in hot ethanol (40 mL) was added aqueous 1.0 N sodium hydroxide (10 mL). The resulting solution was heated to 60° C. and stirred for 4 h. Then, the reaction mixture was cooled down and diluted with EtOAc, washed with 10% HCl and brine. The combined ethyl acetate extracts were dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford 805 mg (97%) of title compound as a light yellow oil. HR-ES(+) m/e calcd for C26H33O8SI (M+H)+ 633.1014, found 633.1008.

Workup

temperatureThen, the reaction mixture was cooled down
washwashed with 10% HCl and brine
dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2da7dbbdd59e4a698949883a6c510278
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093253B2

Reaction notes

Loading…