Sodium Hydroxide → 4-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

HRID 416966Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g, 1.68 mmol) in hot ethanol (40 mL) was added aqueous 2.0 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% aq. HCl and brine. The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to afford 805 mg (89%) of title compound as a light yellow oil. HR-ES(+) calcd for C26H33O7Br [M+Na]+ 559.1302, observed 559.1299.

Workup

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

Sources & evidence

ORD record: ord-df3608967d9343d2b6342931af4b677c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

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