Hydrogen Peroxide → HCID 56646001, compound

HRID 579181Notes

Reaction equation

HRID 579181 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][O:13][C@@:12]([CH2:23][CH:24]=[CH2:25])([CH3:22])[C:11]1=[O:26])=[O:4].B1C2CCCC1CCC2.[OH-:42].[Na+].OO>C1COCC1.CCO>[CH:16]1([C@H:15]2[N:10]([C:9]3[CH:8]=[C:7]([C:27]#[C:28][C:29]([CH3:32])([CH3:30])[CH3:31])[S:6][C:5]=3[C:3]([OH:2])=[O:4])[C:11](=[O:26])[C@:12]([CH2:23][CH2:24][CH2:25][OH:42])([CH3:22])[O:13][CH2:14]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 66684080HCID 66684080, compound

Product 1

HCID 56646001HCID 56646001, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((2R,5R)-2-allyl-5-cyclohexyl-2-methyl-3-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (50 mg, 0.11 mmol, 1.0 equiv) in THF (1.0 mL) was added 9-BBN (0.5 M solution in THF, 0.55 ml, 0.27 mmol, 2.5 equiv) at 0° C. The reaction mixture was then stirred at room temperature for 2 hours. To the solution was then cooled in an ice water bath and was added EtOH, followed by aq. NaOH solution and H2O2 aq. solution. During addition the reaction internal temperature was kept between 5° C. and 10° C. The reaction mixture was then heated to reflux for 90 minutes. After cooled at room temperature, the reaction mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by prep-HPLC to give the product 26 mg. MW: 462.2 [M+H]+. 1H-NMR (400 MHz, MeOD): δ 6.91 (s, 1H), 4.23 (d, 1H), 3.94 (d, 1H), 3.62 (m, 1H), 3.55 (m, 2H), 1.96-1.52 (m, 10H), 1.45 (s, 3H), 1.32 (s, 9H), 1.21 (m, 4H), 1.05 (m, 1H).

Workup

  1. temperatureTo the solution was then cooled in an ice water bath
  2. additionDuring addition the reaction internal temperature
  3. customwas kept between 5° C. and 10° C
  4. temperatureThe reaction mixture was then heated
  5. temperatureto reflux for 90 minutes
  6. temperatureAfter cooled at room temperature
  7. extractionthe reaction mixture was extracted with EtOAc
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-dace6fb9c4a44d3e9c6c353ebeb614cd
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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