Lithium Hydroxide → (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 2405906Notes

Reaction equation

[N:1]([CH2:4][CH2:5][C@@:6]([CH3:16])([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]([O:9]CC)=[O:8])=[N+:2]=[N-:3].[Li+].[OH-]>O>[N:1]([CH2:4][CH2:5][C@@:6]([CH3:16])([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate (3.9 g, 15.6 mmol, 1 eq) in water (7.5 mL) was added LiOH (16 mmol). The mixture was allowed to stir at 80° C. for 16 h. The crude product was then purified by reverse phase chromatography on a 100 g C18 column eluting with a 0-20% MeOH/water gradient (containing 0.5% TFA) to give the desired product (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoic acid (1.2 g, 35% yield). LC-MS: M+H+222.1.

Workup

customThe crude product was then purified by reverse phase chromatography on a 100 g C18 column
washeluting with a 0-20% MeOH/water gradient (containing 0.5% TFA)

Sources & evidence

ORD record: ord-4fe9e1b85e3f494bb1e7fa1b5159eba4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809333B2

Reaction notes

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