Hydrogen Peroxide → HCID 54031872, compound

HRID 1374208Notes

Reaction equation

HRID 1374208 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][C@@H:8]([C:17](N1[C@H](C)[C@H](C2C=CC=CC=2)OC1=O)=[O:18])[CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-:34].OO.CCCCCCC>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:32])[CH2:7][C@H:8]([CH2:9][C@H:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:17]([OH:18])=[O:34])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8900HeptaneHCID 57152232HCID 57152232, compound

Product 1

HCID 54031872HCID 54031872, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

Compound 156 (5.608 b, 12.59 mmol) was dissolved in THF/H2O (60 mL/14 mL) and cooled to 0° C. LiOH (1N, 18.89 mL) and H2O2 (35%, 4.45 mL, 50.4 mmol) were combined, and then added to the reaction dropwise keeping T<5° C. the reaction was stirred at 0° C. for 4 hours, and quenched with Na2SO3 (6.3 g) and NaHSO3 (3.4 g) in 50 mL H2O added dropwise. The reaction was stirred for 15 minutes, and the layers separated. The aqueous layer was extracted with EtOAc (3×100 mL), and the combined extracts dried over MgSO4, filtered, and rotovapped to give an oil. The crude material was dissolved in EtOAc (10 mL) and added dropwise to heptane (250 mL). The suspension was stirred for 20 minutes, and the solids filtered and washed with heptane. The filtrate was washed with 60° C. H2O (100 mL), dried over MgSO4, filtered, and rotovapped to give 157 as an oil (3.52 g). the material was used directly in the next step.

Workup

  1. additionadded to the reaction dropwise keeping T<5° C. the reaction
  2. customquenched with Na2SO3 (6.3 g) and NaHSO3 (3.4 g) in 50 mL H2O
  3. additionadded dropwise
  4. stirringThe reaction was stirred for 15 minutes
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  7. dry with materialthe combined extracts dried over MgSO4
  8. filtrationfiltered
  9. customto give an oil
  10. stirringThe suspension was stirred for 20 minutes
  11. filtrationthe solids filtered
  12. washwashed with heptane
  13. washThe filtrate was washed with 60° C
  14. dry with materialH2O (100 mL), dried over MgSO4
  15. filtrationfiltered

Sources & evidence

ORD record
ord-816c00a2d5964dc6983077e2e6dfbed7
Source dataset
uspto-grants-2007_01
Patent number
US07164034B2

Reaction notes

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