HCID 66975351, compound → HCID 66975769, compound

HRID 1022614Notes

Reaction equation

HRID 1022614 reaction equation
[NH2:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1.[C:25]([O:29][C:30]([N-:32][S:33](N1C=CC(=[N+](C)C)C=C1)(=[O:35])=[O:34])=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(#N)C>[C:25]([O:29][C:30]([NH:32][S:33]([NH:1][CH2:2][C@H:3]1[C@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)[O:8][CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4]1)(=[O:35])=[O:34])=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 66975351HCID 66975351, compoundHCID 178482962HCID 178482962, compound

Product 1

HCID 66975769HCID 66975769, compoundYield 116.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl (6R,7R)-6-(aminomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (100 mg) in acetonitrile (2 mL) was added N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide (181 mg) prepared by the method described in Organic Letters, 2001, 3 (14), 2241-2243, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, distilled water was added to the residue, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (172 mg).

Workup

  1. customprepared by the method
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. distillationdistilled water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-37677fb1aa474ff8a2d3e20b29c7dbcc
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…