Cesium carbonate → HCID 21949732, compound

HRID 2215187Notes

Reaction equation

HRID 2215187 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][Si](C(C)(C)C)(C)C)[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 21949679N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine

Product 1

HCID 21949732HCID 21949732, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

N-(Benzoxazol-2-yl)-N-3-(4-methoxyphenoxy)propyl-3-tert-butyldimethylsilyloxybenzylamine (1.9 g, 3.6 mmol) was dissolved in solvent mixture of N,N-dimethylformamide/H2O (10/1) (5.0 mL). Subsequently, cesium carbonate (1.2 g, 3.6 mmol) was added thereto. The mixture was stirred for 3 hours at room temperature, followed by concentration under reduced pressure. Hydrochloric acid (1.0 mol/L) was added thereto. The resultant mixture was extracted with ethyl acetate, followed by washing the organic layer with brine, drying over anhydrous sodium sulfate, and concentration under reduced pressure. The resultant mixture was subjected to purification by silica gel chromatography (n-hexane/ethyl acetate=5/1), whereby the target compound was obtained (1.3 g, 89%).

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. additionHydrochloric acid (1.0 mol/L) was added
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washby washing the organic layer with brine
  5. dry with materialdrying over anhydrous sodium sulfate, and concentration under reduced pressure
  6. customThe resultant mixture was subjected to purification by silica gel chromatography (n-hexane/ethyl acetate=5/1), whereby the target compound
  7. customwas obtained (1.3 g, 89%)

Sources & evidence

ORD record
ord-916bd44d65a6499789d955fadb4c2667
Source dataset
uspto-grants-2006_09
Patent number
US07109226B2

Reaction notes

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