Hydrogen Peroxide → HCID 14590832, compound

HRID 1722681Notes

Reaction equation

HRID 1722681 reaction equation
[OH:1][C@H:2]([C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[CH:3]=[CH2:4].C12BC(CCC1)CCC2.[OH-:30].[Na+].OO>O1CCCC1.O>[OH:30][CH2:4][CH2:3][C@H:2]([OH:1])[C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 13891107HCID 13891107, compound

Product 1

HCID 14590832HCID 14590832, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The resultant compound from Example 121 (327.6 mg, 1.16 mmol) in tetrahydrofuran (THF, 2 ml) at 0° C. was treated with 9-borabicyclo(3.3.1)nonane (4.6 ml, 2.2 mmol in THF). After 3 h at room temperature water (0.1 ml) then NaOH (280 mg, 7.0 mmol) in water (1 ml) then 30% H2O2 (0.70 ml, 6.9 mmol) were added and the mixture was heated at 50° C. for 90 min. The mixture was concentrated, dissolved in ethyl acetate, washed with brine, dried over Na2SO4, evaporated and chromatographed on silica gel with 2% methanol in chloroform to give 351.1 mg (100%) of the desired compound as an oil. DCI-MS: (M+H)=302.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customchromatographed on silica gel with 2% methanol in chloroform

Sources & evidence

ORD record
ord-5442e7f47d1a4a6bb11df193526b8a60
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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