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

HRID 1022684Notes

Reaction equation

HRID 1022684 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]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][C:10]32[O:12][CH2:11]3)[CH:5]=[CH:6][C:7]=1[Cl:8].[N-:25]=[N+:26]=[N-:27].[Na+].O>CN(C=O)C>[N:25]([CH2:11][C:10]1([OH:12])[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=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]1)=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86663865tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylate

Product 1

HCID 86663868tert-butyl (6RS,7SR)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-6-hydroxy-1,4-oxazepane-4-carboxylateYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylate (460 mg) in DMF (5 ml) was added sodium azide (240 mg), and the mixture was stirred at 80° C. overnight. 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 (232 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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

Sources & evidence

ORD record
ord-0d6dcd61e11c40f9ad46dfb85d858f1a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…