Cesium carbonate → HCID 86588908, compound

HRID 1061221Notes

Reaction equation

HRID 1061221 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:21][CH2:20][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:14][CH2:13]3)=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:13][CH2:14][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:20][CH2:21]3)=[CH:8][CH:7]=2)=[N:4]1)[CH3:34].[CH2:33]([O:32][C:30](=[O:31])[CH2:29][N:4]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:13][CH2:14][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:20][CH2:21]3)=[CH:8][CH:7]=2)=[N:1][N:2]=[N:3]1)[CH3:34]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12183Ethyl iodoacetateHCID 178420598HCID 178420598, compound

Product 2

HCID 86588908HCID 86588908, compoundYield 73%HCID 131723779HCID 131723779, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-[4-(1H-tetrazol-5-yl)-phenyl]-1,4-dioxa-8-aza-spiro[4.5]decane (0.57 g, 2 mmol) (which was obtained in Example 46) in DMF (10 mL) was added cesium carbonate (0.81 g, 2.5 mmol) and ethyl iodoacetate (0.43 g, 2 mmol). The mixture was stirred at room temperature over night, then the reaction was quenched with water, extracted with ethyl acetate. The products from the organic phase was seperated by silica gel chromatography (ethyl acetate/hexanes) to yield ethyl{5-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-2H-tetraazol-2-yl}acetate as a colorless crystal (0.55 g, 73%) and ethyl{5-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-1H-tetraazol-1-yl}acetate as a gum (0.12 g, 16%).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe products from the organic phase was seperated by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1589cb02f20c485bbfee2af31033366e
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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