tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate → tert-butyl (6R,7S)-6-{[(tert-butoxycarbonyl)sulfamoyl]amino}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022622Notes

Reaction equation

HRID 1022622 reaction equation
[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.[C:24]([O:28][C:29]([N-:31][S:32](N1C=CC(=[N+](C)C)C=C1)(=[O:34])=[O:33])=[O:30])([CH3:27])([CH3:26])[CH3:25]>C(#N)C.C(OCC)(=O)C>[C:24]([O:28][C:29]([NH:31][S:32]([NH:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1)(=[O:34])=[O:33])=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 66975508tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylateHCID 178482962HCID 178482962, compound

Product 1

HCID 66976162tert-butyl (6R,7S)-6-{[(tert-butoxycarbonyl)sulfamoyl]amino}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylateYield 44.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (300 mg) in acetonitrile (5 mL) was added N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (375 mg) prepared by the method described in Organic Letters, 3 (14), 2241-2243 (2001), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (200 mg).

Workup

  1. customprepared by the method
  2. washThe diluted solution was washed with distilled water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1e296a80eeb04bc198047c3951a11c8b
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…