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

HRID 28430Notes

Reaction equation

HRID 28430 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 (3S,5R)-5-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-octanoic acid tert-butyl ester (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 (S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl ester (6 g, 93%) which was used immediately 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-f8d42b5a854448ea8b44915fe32b4289
Source dataset
uspto-grants-2008_09
Patent number
US07419981B2

Reaction notes

Loading…