Water → tert-butyl (6RS,7SR)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-6-methoxy-1,4-oxazepane-4-carboxylate

HRID 1022685Notes

Reaction equation

HRID 1022685 reaction equation
[H-].[Na+].[N:3]([CH2:6][C:7]1([OH:29])[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8]1)=[N+:4]=[N-:5].[CH3:30]I.O>CN(C=O)C>[N:3]([CH2:6][C:7]1([O:29][CH3:30])[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[O:12][CH2:11][CH2:10][N:9]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:8]1)=[N+:4]=[N-:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86663868tert-butyl (6RS,7SR)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate

Product 1

HCID 86663869tert-butyl (6RS,7SR)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-6-methoxy-1,4-oxazepane-4-carboxylateYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, sodium hydride (60% oil, 8 mg) was added to a solution of tert-butyl (6RS,7SR)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylate (120 mg) in DMF (5 mL). The mixture was stirred at room temperature for 20 min, methyl iodide (122 mg) was added, and the mixture was stirred at the same temperature for 30 min. 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 (115 mg).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at the same temperature for 30 min
  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-8ea9e2d99a4946e585452352cebb4fa0
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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