Hydrogen Peroxide → (S)-2-((R)-2-Methyl-butyl)-succinic Acid 4-tert-butyl Ester

HRID 2216668Notes

Reaction equation

HRID 2216668 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][C@@H:8]([C:14](N1[C@H](C)[C@H](C2C=CC=CC=2)OC1=O)=[O:15])[CH2:9][C@H:10]([CH3:13])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].OO.S(=O)(O)[O-:35].[Na+].S([O-])([O-])=O.[Na+].[Na+]>O.C1COCC1>[C:1]([O:5][C:6](=[O:29])[CH2:7][C@H:8]([CH2:9][C@H:10]([CH3:13])[CH2:11][CH3:12])[C:14]([OH:15])=[O:35])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 23665763Sodium BisulfiteHCID 66939639(3S,5R)-5-Methyl-3-[1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-methanoyl]-heptanoic acid tert-butyl ester

Product 1

HCID 54311211(S)-2-((R)-2-Methyl-butyl)-succinic Acid 4-tert-butyl EsterYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

(3S,5R)-5-Methyl-3-[1-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-methanoyl]-heptanoic acid tert-butyl ester (7.26 g, 0.018 mol) in H2O (53 mL) and THF (176 mL) at 0° C. was added a premixed solution of LiOH (37 mL of a 0.8 M solution) and H2O2 (10.57 mL of a 30% solution) and the solution warmed to room temperature. After 2 hours sodium bisulfite (7 g), sodium sulfite (13 g), and water (60 mL) was added and the two layers were separated and the aqueous layer extracted with ether. The combined organic phases were concentrated to an oil that was dissolved in heptane (200 mL). The resultant solid was filtered off and the filtrate dried (MgSO4) and concentrated to afford the titled compound as an oil (4.4 g) that was used without further purification. MS, m/z (relative intensity): 243 [100%]; 1H NMR (400 MHz; CDCl3) δ2.88 (m, 1H), 2.59 (m, 1H), 2.36 (m, 1H), 1.65 (m, 1H), 1.41 (s, 9H), 1.20 (m, 4H), 0.84 (m, 6H).

Workup

  1. customthe two layers were separated
  2. extractionthe aqueous layer extracted with ether
  3. concentrationThe combined organic phases were concentrated to an oil that
  4. dissolutionwas dissolved in heptane (200 mL)
  5. filtrationThe resultant solid was filtered off
  6. dry with materialthe filtrate dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1a09a0b2bc554e01a6ae6f9bd47eff33
Source dataset
uspto-grants-2006_09
Patent number
US07112610B2

Reaction notes

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