3-(3-Bromo-1,4-dioxonaphthalen-2-yl)propanoic acid → (2R/S)-3-(3-bromo-1,4-naphthoquinon-2-yl)-2-methylpropionic acid

HRID 1527716Notes

Reaction equation

HRID 1527716 reaction equation
[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[CH2:14][CH:15]([CH3:21])[C:16]([O:18]CC)=[O:17].BrC1C(=O)C2C(=CC=CC=2)C(=O)C=1CCC(O)=O>CC(C)=O>[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:13])[C:3]=1[CH2:14][CH:15]([CH3:21])[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 454872363-(3-Bromo-1,4-dioxonaphthalen-2-yl)propanoic acidHCID 70835151Ethyl (2R/S)-3-(3-bromo-1,4-naphthoquinon-2-yl)-2-methylpropionate

Product 1

HCID 59583711(2R/S)-3-(3-bromo-1,4-naphthoquinon-2-yl)-2-methylpropionic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 69b was prepared from racemic 68b (0.027 g, 0.08 mmol) as described above for 69a to give 0.016 g (0.05 mmol, 63%) of the product as a yellow solid following flash chromatography (1:4 acetone:hexanes 0 to 0.5% AcOH) and recrystallization from Et2O/hexanes.

Workup

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Sources & evidence

ORD record
ord-665a1d651c3a4d16868285ecab5507f0
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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