Tert-butyl 3-hydroxyazetidine-1-carboxylate → HCID 117667172, compound

HRID 1526229Notes

Reaction equation

HRID 1526229 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.C[C:14]([CH3:17])([O-:16])[CH3:15].[K+].[Cl:19][C:20]1[C:21]([C:29]([NH2:31])=[O:30])=[N:22][C:23]([CH2:27][CH3:28])=[C:24](Cl)[N:25]=1>CN(C)C=O>[CH:14]([O:16][CH:2]([CH3:5])[CH3:3])([CH3:17])[CH3:15].[C:29]([C:21]1[N:22]=[C:23]([CH2:27][CH3:28])[C:24]([O:1][CH:2]2[CH2:3][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5]2)=[N:25][C:20]=1[Cl:19])(=[O:30])[NH2:31]

Participants

6

Reactant 3

HCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 848199603,5-Dichloro-6-ethylpyrazine-2-carboxamide

Product 2

HCID 7914Diisopropyl EtherHCID 117667172HCID 117667172, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate (420 mg) and N,N-dimethylformamide (12.5 mL) was added potassium tert-butoxide (260 mg) under ice-cooling, followed by stirring for 1 hour, and then 3,5-dichloro-6-ethylpyrazine-2-carboxamide (500 mg) was added thereto, followed by stirring for 1 hour. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate), and then washed with a mixed solvent of hexane:diisopropyl ether to obtain tert-butyl 3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]azetidine-1-carboxylate (318 mg) as a white solid.

Workup

  1. temperaturecooling
  2. stirringby stirring for 1 hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate)
  8. washwashed with a mixed solvent of hexane

Sources & evidence

ORD record
ord-a7721f856b0648f7895d5594f0d71b08
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

Loading…