Hydrogen Peroxide → HCID 67892238, compound

HRID 373774Notes

Reaction equation

HRID 373774 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:16](=[CH:17][C:18]([Br:22])=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]1=[O:23])=[O:5])[CH3:2].[OH:24]O>C(O)(=O)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:21]2[C:16](=[CH:17][C:18]([Br:22])=[CH:19][CH:20]=2)[NH:15][C:14](=[O:24])[C:13]1=[O:23])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 67770303HCID 67770303, compound

Product 1

HCID 67892238HCID 67892238, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The above ester (3.43 g, 9.0 mmol) was reacted with 30% H2O2 (14.9 ml) in glacial acetic acid (40 ml) at 55° C. for 20h. The mixture was poured onto crushed ice (250 ml) and extracted with ethyl acetate (2×400 ml). The combined organic extract was washed with half saturated sodium hydrogen carbonate solution and water, dried (Na2SO4), evaporated to dryness and stripped with ether. The product was triturated with heptane (20 ml) overnight, the precipitate filtered off, washed with heptane and dried to afford 2.86 g of the title compound. M.p. 187°-190° C. 1H-NMR(DMSO-d6):δ0.80(m, 3H), 1.1(t, 3H), 1.12-1.4(m, 6H) 1.9-2.25(m, 2H), 4.0-4.17(m, 2H), 5.2-5.7(m, 3H), 12.28(s, 1H).

Workup

  1. additionThe mixture was poured
  2. extractionextracted with ethyl acetate (2×400 ml)
  3. extractionThe combined organic extract
  4. washwas washed with half saturated sodium hydrogen carbonate solution and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness
  7. customThe product was triturated with heptane (20 ml) overnight
  8. filtrationthe precipitate filtered off
  9. washwashed with heptane
  10. customdried

Sources & evidence

ORD record
ord-61b232201e8a4fc0adccd0a90af47d0f
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

Loading…