Lithium hydroxide, monohydrate → 3-((1S)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]benzoic acid

HRID 20488Notes

Reaction equation

O.[OH-].[Li+].[Si:4]([O:11][CH2:12][C@H:13]([CH3:36])[O:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[CH:24]=1)[C:18]([O:20]C)=[O:19])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]>C1COCC1.O>[Si:4]([O:11][CH2:12][C@H:13]([CH3:36])[O:14][C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:33])=[O:34])=[CH:28][CH:27]=2)[CH:24]=1)[C:18]([OH:20])=[O:19])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 45 °C

Procedure

Lithium hydroxide monohydrate (346 mg, 8.24 mmol) was added to a solution of methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]benzoate (3.70 g, 7.49 mmol) in THF (50 mL) and water (10 mL) and the reaction stirred for 2 h. A further portion of lithium hydroxide monohydrate (346 mg, 8.24 mmol) was then added and the reaction was heated at 45° C. for 1.5 h. The THF was then evaporated and water layer was extracted with diethyl ether (10 mL). The remaining aqueous layer was acidified with 5% w/v aqueous citric acid and extracted (2×50 mL) with ethyl acetate and the combined organic layers were dried (MgSO4), filtered and evaporated to afford the title compound as a gum (2.54 g, 71%).

Workup

customThe THF was then evaporated
extractionwater layer was extracted with diethyl ether (10 mL)
extractionextracted (2×50 mL) with ethyl acetate
dry with materialthe combined organic layers were dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-4a82ea0189664ddbbbe2d51f548d35ac
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745475B2

Reaction notes

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