Lithium hydroxide, monohydrate → HCID 67188853, compound

HRID 546155Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([CH3:22])[CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.O.[OH-].[Li+]>O1CCCC1.C(O)C.O.S([O-])(O)(=O)=O.[K+]>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[C:3]([OH:23])=[O:2])=[CH:13][C:14]=1[CH3:22])(=[O:20])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

2-(4-Methanesulfonyl-3-methyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (1.30 g, 3.82 mmol) was dissolved in tetrahydrofuran:ethanol:water (6:3:2) reaction (50 mL) and treated with lithium hydroxide monohydrate (800 mg, 19.1 mmol) at 25° C. It was stirred at 25° C. for 2 h. The reaction was then diluted with a 1 M aqueous solution of potassium hydrogen sulfate (100 mL) and then extracted with ethyl acetate (1×200 mL), the organic layer was then dried over sodium sulfate, filtered and concentrated in vacuo with silica gel (2 g) and purified by Biotage Flash Chromatography (40S column, Silica gel, 10% methanol/ethyl acetate) to afford 2-(4-methanesulfonyl-3-methyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid (1.15 g, 92%) as a colorless oil.

Workup

customreaction (50 mL)
extractionextracted with ethyl acetate (1×200 mL)
dry with materialthe organic layer was then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo with silica gel (2 g)
custompurified by Biotage Flash Chromatography (40S column, Silica gel, 10% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-770ad6b521b449b08ebfc9aa00e20633
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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