Hydrochloric Acid → 4-[3-[6-(3-Benzylcarbamoyl-5-iodo-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric Acid

HRID 1670072Notes

Reaction equation

C([O:3][C:4](=[O:46])[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]([I:28])[CH:25]=[C:24]([C:29](=[O:38])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:23]=2)[C:10]=1[CH2:39][CH2:40][C:41]([O:43]CC)=[O:42])C.[OH-].[Na+].Cl>C1COCC1>[CH2:31]([NH:30][C:29]([C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([I:28])[CH:25]=1)[O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:11]1[C:10]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:46])=[O:3])=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-[3-[6-(3-Benzylcarbamoyl-5-iodo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (8.7 g) was dissolved in THF (30 mL) and 2 M NaOH was added (30 mL). The resulting heterogeneous mixture was stirred vigorously at 55° C. for 4 h. Then it was acidified with 3 N HCl and extracted into diethyl ether. Etherate extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to produce 8.1 g (100% yield) of colorless oil which solidified upon standing.

Workup

extractionextracted into diethyl ether
extractionEtherate extract
washwas washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-768ba9ba868c480498bb55fcb16a6b24
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989454B2

Reaction notes

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