Hydrochloric Acid → E-3-[1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoic acid

HRID 350091Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])=[CH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:35]([O:34][C:32]1[CH:31]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:14]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 50 °C

Procedure

After a mixture of ethyl(E)-3-[1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoate (544 mg), 1N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (6 ml) and ethanol (6 ml) was stirred overnight at 50° C., and 1N hydrochloric acid (2 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystal obtained was filtered, and E-3-[1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]propenoic acid (479 mg, yield: 93%) was obtained. This was recrystallized from ethanol. Melting point: 182–183° C.

Workup

extractionwas extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated
customThe colorless crystal obtained
filtrationwas filtered

Sources & evidence

ORD record: ord-1158ae63880a459ea35af6bee0e3d8da
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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