Water → HCID 89500577, compound

HRID 2178510Notes

Reaction equation

HRID 2178510 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=1.[OH:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1.O>CS(C)=O.[Cl-].[Na+].O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([O:15][CH:16]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19]2)=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 27628712,5-DifluoropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 89500577HCID 89500577, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Potassium tert-butoxide (1M in THF, 14.4 ml, 14.4 mmol, 5 eq) and 2,5-difluoropyridine (498.3 mg, 4.33 mmol, 1.5 eq) are added to a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate a1-47 (500 mg, 2.89 mmol, 1 eq) in DMSO (50 ml). The reaction is stirred for 4 h at room temperature. Brine (70 ml) and water (10 ml) are added. The resulting mixture is extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. The residue of evaporation is purified by flash chromatography over silicagel (eluent: EtOAc/Heptane 10/90) to afford 240 mg of tert-butyl 3-[(5-fluoropyridin-2-yl)oxy]azetidine-1-carboxylate a1-48.

Workup

  1. extractionThe resulting mixture is extracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue of evaporation
  6. customis purified by flash chromatography over silicagel (eluent: EtOAc/Heptane 10/90)

Sources & evidence

ORD record
ord-0b3446b1ddef466fbe3af49541e4ec42
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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