Acetic Acid → 3-[3-(2-oxo-2-propoxyethyl)-1H-indol-2-yl]propanoic acid

HRID 476224Notes

Reaction equation

[OH-].[K+].[O:3]=[C:4]([O:23][CH2:24][CH2:25][CH3:26])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:15][CH2:16][C:17]([O:19]CCC)=[O:18].C(O)(=O)C>C(O)CC>[O:3]=[C:4]([O:23][CH2:24][CH2:25][CH3:26])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

Aqueous 8N KOH (1.05 equiv.) was added to a stirred solution of propyl 3-[3-(2-oxo-2-propoxyethyl)-1H-indol-2-yl]propanoate from Step 2 in n-propanol (0.5 M). The mixture was stirred at 50° C. for 4 h. The reaction mixture was cooled to rt, quenched with acetic acid (1.2 equiv.) and concentrated. The residue was purified on a pad of silica gel using CH2Cl2, then CH2Cl2/EtOAc (9/1) and finally CH2Cl2/EtOAc/MeOH (88/10/2) to afford after evaporation of the volatiles, the desired material (68%) as yellow oil.

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated
customThe residue was purified on a pad of silica gel
customCH2Cl2/EtOAc (9/1) and finally CH2Cl2/EtOAc/MeOH (88/10/2) to afford
customafter evaporation of the volatiles

Sources & evidence

ORD record: ord-2cde1184a77c4bf38b3027e3f1df1970
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637671B2

Reaction notes

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