Hydrogen Peroxide → (S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl ester

HRID 458032Notes

Reaction equation

HRID 458032 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][C@@H:8]([C:15](N1[C@H](C)[C@H](C2C=CC=CC=2)OC1=O)=[O:16])[CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].OO.S(=O)(O)[O-:36].[Na+].S([O-])([O-])=O.[Na+].[Na+]>O.C1COCC1.CCOCC.CCCCCC>[C:1]([O:5][C:6](=[O:30])[CH2:7][C@H:8]([CH2:9][C@H:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[C:15]([OH:16])=[O:36])([CH3:2])([CH3:3])[CH3:4]

Participants

10

Reactant 5

HCID 784Hydrogen Peroxide2×HCID 3939Lithium Hydroxide2×HCID 24437Sodium SulfiteHCID 23665763Sodium BisulfiteHCID 57207445(3S,5R)-5-Methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-octanoic acid tert-butyl ester

Product 1

HCID 21031299(S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl esterYield 93%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To ester 101 (10.8 g, 0.025 mol) in H2O (73 mL) and THF (244 mL) at 0° C. was added a premixed solution of LiOH (51.2 mL of a 0.8 M solution) and H2O2 (14.6 mL of a 30% solution). After 4 hours a further 12.8 mL LiOH (0.8 M solution) and 3.65 mL of H2O2 (30% solution) was added. After 30 minutes sodium bisulfite (7 g), sodium sulfite (13 g), and water (60 mL) was added followed by hexane (100 mL) and ether (100 mL). 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 (300 mL). The resultant solid was filtered off and the filtrate dried (MgSO4) and concentrated to afford an oil (6 g, 93%) which was used without further purification. MS, m/z (relative intensity): 257 [M+H, 100%].

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 (300 mL)
  5. filtrationThe resultant solid was filtered off
  6. dry with materialthe filtrate dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36f8a9e9c2fe41f699e43ff2af43b303
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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