Lithium Hydroxide → (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoic acid

HRID 533507Notes

Reaction equation

HRID 533507 reaction equation
[CH3:1][C@@:2]([S:25]([CH3:28])(=[O:27])=[O:26])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Li+].BrC1C=CC(CCC(C)(S(C)(=O)=O)C(O)=O)=CC=1>>[CH3:1][C@@:2]([S:25]([CH3:28])(=[O:26])=[O:27])([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([B:16]2[O:20][C:19]([CH3:21])([CH3:22])[C:18]([CH3:23])([CH3:24])[O:17]2)=[CH:14][CH:15]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 66577906(+/-)-4-(4-Bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acidHCID 66577950ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate

Product 1

HCID 66578010(2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoic acidYield 76%

Procedure

The title compound (7.4 g, 76%) was prepared from ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate (10.5 g, 25.6 mmol) and lithium hydroxide (4.3 g, 102 mmol) by a procedure analogous to that described for (+/−)-4-(4-bromophenyl)-2-methyl-2-(methylsulfonyl)butanoic acid as in Preparation 3 step B. LCMS m/z 381.6 (M−1).

Sources & evidence

ORD record
ord-0860c96279d5451d8e2e9fda8f12ec2a
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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