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

HRID 458032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458032
[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]

Komponenten

10

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

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%].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-36f8a9e9c2fe41f699e43ff2af43b303
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189747B2

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