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

HRID 28430노트

반응식

HRID 28430 반응식
[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]

참가 물질

10

반응물 5

HCID 784Hydrogen Peroxide2회HCID 3939Lithium Hydroxide2회HCID 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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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%].

후처리

  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

출처 및 근거

ORD 기록
ord-f8d42b5a854448ea8b44915fe32b4289
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419981B2

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