Sodium Hydroxide → HCID 57867424, compound

HRID 1930771Notes

Reaction equation

HRID 1930771 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH2:19]O)[CH:15]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:24])=O.N1C2C=CC=CC=2N=N1.[OH-].[Na+].C(OC)(C)(C)C>CN(C)C(=O)C>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[C:13]([C:14]2[O:18][N:17]=[C:16]([CH2:19][Cl:24])[CH:15]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 57867422HCID 57867422, compoundHCID 178527217HCID 178527217, compound2×

Product 1

HCID 57867424HCID 57867424, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

Under a nitrogen atmosphere, tert-butyl{3-[3-(hydroxymethyl)isoxazol-5-yl]pyridin-2-yl}carbamate (781 mg, 2.68 mmol) was dissolved in N,N-dimethylacetamide (2.7 mL). To the solution was added the above solution of thionyl chloride-benzotriazole (1:1.1) in N,N-dimethylacetamide (6 mL, 14.4 mmol) dropwise under an ice water cooling, which was stirred at the same temperature for one hour and then stirred at room temperature. After one hour and 20 minutes, under the ice water cooling, a solution of thionyl chloride-benzotriazole (1:1.1) in N,N-dimethylacetamide (2.2 mL, 5.12 mmol) was added dropwise thereto, and the solution was stirred at room temperature for one hour. Under the ice water cooling, to the reaction solution were added 1N aqueous sodium hydroxide and tert-butylmethylether to adjust basic and then extracted. The organic layer was washed sequentially with 0.5N aqueous sodium hydroxide and 5% sodium chloride water, dried over anhydrous magnesium sulfate and then the solvent was evaporated under a reduced pressure to obtain a crude body of the title compound (953 mg) as a pale yellow oily product.

Workup

  1. stirringstirred at room temperature
  2. waitAfter one hour
  3. stirringthe solution was stirred at room temperature for one hour
  4. extractionextracted
  5. washThe organic layer was washed sequentially with 0.5N aqueous sodium hydroxide and 5% sodium chloride water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-0eac76fa00d940af9b9994249152e7a3
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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