Hydrogen Peroxide → (S)-2-(2,2-Dimethyl-pentyl)-succinic acid 4-tert-butyl ester

HRID 2216677Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[CH2:7][CH:8]([C:16](N1C(C)C(C2C=CC=CC=2)OC1=O)=[O:17])[CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-:33].OO>>[C:1]([O:5][C:6](=[O:31])[CH2:7][C@H:8]([CH2:9][C:10]([CH3:14])([CH3:15])[CH2:11][CH2:12][CH3:13])[C:16]([OH:17])=[O:33])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 3

HCID 784Hydrogen Peroxide

HCID 3939Lithium Hydroxide

HCID 688534665,5-Dimethyl-3-(4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-octanoic acid tert-butyl ester

Product 1

HCID 86589981(S)-2-(2,2-Dimethyl-pentyl)-succinic acid 4-tert-butyl esterYield 112.5%

Procedure

According to example 1, 3.4 g (7.9 mmol) of 5,5-dimethyl-3-(4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-octanoic acid tert-butyl ester, 16 mL (12.8 mmol) of 0.8N LiOH and 4.5 mL of 30% H2O2 gave 2.42 g (>100%) of the title compound as an oil. 1HNMR (400 MHz; CDCl3): 0.77–0.82 (m, 9H), 1.14–1.29 (m, 5H), 1.42 (s, 9H), 1.77 (dd, 1H, J=8 Hz, 16 Hz), 2.36 (dd, 1H, J=6 Hz, 16 Hz), 2.59 (dd, 1H, J=8 Hz, 16 Hz), 2.75–2.85 (m, 1H).

Sources & evidence

ORD record: ord-365f24a753bc494084133eebb3d92236
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112610B2

Reaction notes

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