Hydrogen Peroxide → HCID 54248964, compound

HRID 1767095Notes

Reaction equation

HRID 1767095 reaction equation
OO.O.[OH-].[Li+].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][CH2:20][C:21](N(C(OC(C)(C)C)=O)C2C3C(=CC=C(OC)C=3)N=CC=2)=[O:22])[C@@H:15]([CH:43]=[CH2:44])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].S([O-])([O-])=[O:46].[Na+].[Na+]>O1CCCC1.O>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][CH2:20][C:21]([OH:22])=[O:46])[C@@H:15]([CH:43]=[CH2:44])[CH2:14]1)=[O:12])([CH3:7])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 69345817HCID 69345817, compound

Product 1

HCID 54248964HCID 54248964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.26 cm3 of an aqueous solution of hydrogen peroxide at 9.8 mol/l and 0.310 g of lithium hydroxide monohydrate are added successively, at a temperature in the region of 20° C., under an argon atmosphere, to 2 g (3.7 mmol) of (3R,4R)-1-tert-butyloxycarbonyl-4-{3-[tert-butyloxycarbonyl-(6-methoxyquinolin-4-yl)amino]-3-oxopropyl}-3-vinylpiperidine in solution in 56 cm3 of tetrahydrofuran and 18 cm3 of water. After stirring for 16 hours, 50 cm3 of a saturated aqueous sodium sulfite solution are added and the tetrahydrofuran is then evaporated off under reduced pressure (2.7 kPa). The aqueous phase is filtered and the residue is washed with 3 times 30 cm3 of water. The filtrates are pooled, acidified to a pH in the region of 3.5 by adding acetic acid and then extracted with 3 times 40 cm3 of dichloromethane. The organic phases are pooled, dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.9 g of (3R,4R)-1-tert-butyloxycarbonyl-4-(2-carboxyethyl)-3-vinylpiperidine in the form of a colorless oil.

Workup

  1. customthe tetrahydrofuran is then evaporated off under reduced pressure (2.7 kPa)
  2. filtrationThe aqueous phase is filtered
  3. washthe residue is washed with 3 times 30 cm3 of water
  4. additionby adding acetic acid
  5. extractionextracted with 3 times 40 cm3 of dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-e2ee1a24e22040df9075c55fb711e108
Source dataset
uspto-grants-2007_06
Patent number
US07232834B2

Reaction notes

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