Hydrochloric Acid → 3-(4-t-Butyldimethylsilyloxybenzyl)-2-ethyl-2-hydroxysuccinic acid

HRID 1774377Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][CH:14]([C:24]([O:26]CC)=[O:25])[C:15]([CH2:22][CH3:23])([OH:21])[C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Li+].Cl>O1CCOCC1.C(OCC)(=O)C>[Si:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][CH:14]([C:24]([OH:26])=[O:25])[C:15]([CH2:22][CH3:23])([OH:21])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of diethyl 3-(4-t-butyldimethylsilyloxybenzyl)-2-ethyl-2-hydroxysuccinate 425 mg (0.968 mmol) in 1,4-dioxane (3.9 mL) was added 1 M lithium hydroxide aqueous solution (3.9 mL, 3.9 mmol) at room temperature, and the mixture was stirred at 60° C. for 22 h. The reaction mixture was adjusted to pH 1 with 1 M hydrochloric acid with stirring under ice cooling. The solvent was evaporated under reduced pressure, and the residue thus obtained was dissolved in ethyl acetate, and washed with water and brine. The organic layer was concentrated under reduced pressure and dried in vacuum to give 343 mg (crude) of 3-(4-t-butyldimethylsilyloxybenzyl)-2-ethyl-2-hydroxysuccinic acid as a solid.

Workup

stirringwith stirring under ice cooling
customThe solvent was evaporated under reduced pressure
customthe residue thus obtained
washwashed with water and brine
concentrationThe organic layer was concentrated under reduced pressure
customdried in vacuum

Sources & evidence

ORD record: ord-779a52dd3449409791d5e20e0483f392
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260375B2

Reaction notes

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