Water → Benzyl 6-((ethoxycarbonyl)methyl)pyridin-3-ylcarbamate

HRID 714912Notes

Reaction equation

HRID 714912 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][N:7]=1)[CH3:2].N1C=CC=CC=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:8][N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 21876034Ethyl 2-(5-aminopyridin-2-yl)acetate

Product 1

HCID 131734078Benzyl 6-((ethoxycarbonyl)methyl)pyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(5-aminopyridin-2-yl)acetate (2.0 g) in tetrahydrofuran (30 mL) were successively added pyridine (2.7 mL) and benzyl chloroformate (1.9 mL) in an ice bath, and the mixture was stirred at the same temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.6 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c06f06eb5ca143c29619e6caa2443781
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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