Lithium hydroxide, monohydrate → HCID 90386883, compound

HRID 2170233Notes

Reaction equation

HRID 2170233 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5]([C:18]([O:20]CC)=O)=[C:6]([CH3:17])[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1.O.[OH-].[Li+]>C(O)C.O>[CH3:17][C:6]1[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[C:4]2[CH2:3][CH2:2][NH:1][C:18](=[O:20])[C:5]=12

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90387514HCID 90387514, compound

Product 1

HCID 90386883HCID 90386883, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of Example 93e (3.36 g, 10.29 mmol) and lithium hydroxide monohydrate (3.17 g, 76 mmol) in ethanol (47.5 mL) and water (2.5 mL) was added to 100 mL microwave reaction vessel with stir bar. The mixture was heated at 120° C. for 30 minutes in a Ethos Microsynth multimode microwave reactor (Milestone Inc.), then cooled to ambient temperature. The reaction mixture was added to 200 mL water and stirred for 15 minutes. The mixture extracted with 3×200 mL 10% methanol/dichloromethane and the combined dichloromethane extracts dried over anhydrous sodium sulfate. Filtration and solvent removal provided a brown oil which was chromatographed on a 40 g silica cartridge eluting with 0-10% methanol/dichloromethane to provide the title compound.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringstirred for 15 minutes
  3. extractionThe mixture extracted with 3×200 mL 10% methanol/dichloromethane
  4. dry with materialthe combined dichloromethane extracts dried over anhydrous sodium sulfate
  5. filtrationFiltration and solvent removal
  6. customprovided a brown oil which
  7. customwas chromatographed on a 40 g silica cartridge
  8. washeluting with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-748eb369fda946a6b35fcb5419613918
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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