Hydrochloric Acid → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid

HRID 1818468Notes

Reaction equation

C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH2:29][CH2:30][CH3:31])[CH:12]=2)[CH:5]=1.O.[OH-].[Li+].Cl>O1CCCC1.CO.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([S:18][CH2:17][C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:32])=[O:2])=[C:20]([CH2:29][CH2:30][CH3:31])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenylsulfanylmethyl)-benzyl]-benzoic acid methyl ester (238 mg, 0.53 mmol) in tetrahydrofuran (5 ml) and methanol (4 ml). Add lithium hydroxide monohydrate (89 mg, 2.1 mmol) and water (1.5 ml), then stir at room temperature for 18 hours. Cool at 0° C. and adjust to pH 3 with 1 N hydrochloric acid. Dilute with water (35 ml) and extract with ethyl acetate (2×20 ml). Combine the organic extracts, dry over sodium sulfate, filter and concentrate to a solid. Purify the crude product via reverse phase HPLC using a gradient of 90:10 to 20:80 (water/0.1% TFA):acetonitrile as eluent to give the title compound (196 mg, 85%).

Workup

extractionextract with ethyl acetate (2×20 ml)
dry with materialCombine the organic extracts, dry over sodium sulfate
filtrationfilter
concentrationconcentrate to a solid
customPurify the crude product via reverse phase HPLC

Sources & evidence

ORD record: ord-6b831f9697444a9f9eb09fc5d6f897cf
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598423B2

Reaction notes

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