Hydrochloric Acid → HCID 15840675, compound

HRID 342771Notes

Reaction equation

[CH2:1]([C:4]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][S:17]C(C2C=CC=CC=2)C([O-])=O)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[CH2:2][CH3:3].[OH-:35].[K+].[CH3:37][OH:38].[ClH:39]>CO.O>[Cl:39][C:9]1[CH:5]=[C:4]([CH2:1][C:37]([OH:38])=[O:35])[CH:12]=[CH:11][C:10]=1[S:17][CH2:16][CH2:15][CH2:14][O:13][C:12]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 30 °C

Procedure

Methyl 3-chloro-4-(3-(4-propyl-N-(4-chlorophenyl)-5-indoleoxy)propylthiophenyl-acetate (Step F; 100 mg, 0.18 mmol) was taken up in 3 mL methanol:water (2:1). To this was added a 0.5M solution of potassium hydroxide in methanol (1.80 mL, 0.90 mmol). The reaction was heated to 30° C. for 2 hours at which time the mixture was acidified to pH 3 with 1M hydrochloric acid. The aqueous solution was extracted with ethyl acetate and the organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (30% ethyl acetate/hexane/1% acetic acid) to provide the title compound as a golden oil which solidifies upon pumping.

Workup

extractionThe aqueous solution was extracted with ethyl acetate
washthe organic layer was washed with water, brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customthe crude residue purified by flash chromatography on silica gel (30% ethyl acetate/hexane/1% acetic acid)

Sources & evidence

ORD record: ord-3076b414b7d54c2aa741beee5376ccd6
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859051

Reaction notes

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