Ethyl Acetate → HCID 22063832, compound

HRID 1828178Notes

Reaction equation

HRID 1828178 reaction equation
[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([CH:15]([OH:31])[CH:16]([NH:24][C:25](=[O:30])[CH2:26][CH2:27][O:28][CH3:29])[C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[CH:14][C:9]=3[N:8]([CH3:32])[C:7]2=[O:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:1]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([C:15](=[O:31])[CH:16]([NH:24][C:25](=[O:30])[CH2:26][CH2:27][O:28][CH3:29])[C:17]4[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=4)=[CH:14][C:9]=3[N:8]([CH3:32])[C:7]2=[O:33])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 22063871HCID 22063871, compound

Product 1

HCID 22063832HCID 22063832, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

N-[2-(1-Cyclopentyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-2-hydroxy-1-m-tolyl-ethyl]-3-methoxy-propionamide (433 mg, 0.96 mmol) was dissolved in methylene chloride (9.6 mL) and N-methylmorpholine N-oxide (168.7 mg, 1.44 mmol) was added. After stirring for ten minutes, TPAP (20.2 mg, 0.06 mmol) was added. The reaction was stirred for 1 hour, after which time LCMS and TLC (ethyl acetate) indicated complete reaction. The reaction mixture was poured into saturated aqueous sodium bicarbonate and additional methylene chloride was added. The organic phase was separated and washed with brine, followed by aqueous copper sulfate. The organic phase was then filtered through a plug of silica gel, eluting with ethyl acetate. Concentration of the filtrate afforded 294 mg of a white X solid that was used without further purification.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. customreaction
  3. additionwas added
  4. customThe organic phase was separated
  5. washwashed with brine
  6. filtrationThe organic phase was then filtered through a plug of silica gel
  7. washeluting with ethyl acetate
  8. customConcentration of the filtrate afforded 294 mg of a white X solid that
  9. customwas used without further purification

Sources & evidence

ORD record
ord-9e2ce73698b042c3a996a6ca66856b26
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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