Sodium Iodide → HCID 66976194, compound

HRID 1022722Notes

Reaction equation

HRID 1022722 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH:12]2[OH:25])[CH:7]=[CH:8][C:9]=1[Cl:10].Cl[C:27]1[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH:28]=1.[I-].[Na+]>CN(C=O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][CH:12]2[O:25][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[N:32]=2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 242723Methyl 6-chloropicolinateHCID 66975075tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976194HCID 66976194, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, sodium hydride (60% in oil, 53 mg) was added to a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (400 mg) in DMF (5 mL). After stirring at room temperature for 20 min, methyl 6-chloropicolinate (280 mg) and sodium iodide (330 mg) were added, and the mixture was stirred at the same temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (207 mg).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at the same temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-035657dbe8bf48f9af30c12d3cdf11f7
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…