Dimethyl Sulfoxide → methyl 3-(4-((11-oxodibenzo[b,f][1,4]oxazepin-10(11H)-yl)methyl)-1H-1,2,3-triazol-1-yl)propanoate

HRID 718105Notes

Reaction equation

HRID 718105 reaction equation
Br[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].CS(C)=O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[CH2:25]([N:28]1[C:34](=[O:35])[C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[O:31][C:30]2[CH:40]=[CH:41][CH:42]=[CH:43][C:29]1=2)[C:26]#[CH:27].[N-:44]=[N+:45]=[N-:46].[Na+]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2].C(OCC)(=O)C.O>[O:35]=[C:34]1[C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[O:31][C:30]2[CH:40]=[CH:41][CH:42]=[CH:43][C:29]=2[N:28]1[CH2:25][C:26]1[N:44]=[N:45][N:46]([CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:27]=1

Participants

10

Reactant 5

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 76934Methyl 3-bromopropanoateHCID 23667548Sodium AscorbateHCID 5978344810-(prop-2-ynyl)dibenzo[b,f][1,4]oxazepin-11(10H)-one

Product 1

HCID 59783857methyl 3-(4-((11-oxodibenzo[b,f][1,4]oxazepin-10(11H)-yl)methyl)-1H-1,2,3-triazol-1-yl)propanoateYield 31%

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-bromopropanoate (0.227 g, 1.37 mmol) was dissolved in a solution of sodium azide in DMSO (0.5M, 2.7 mL, 1.37 mmol). The reaction mixture was stirred at room temperature for 3 hours. Water (3.0 mL), followed by sodium ascorbate (0.027 g, 0.137 mmol), followed by compound 434 (0.340 g, 1.37 mmol), followed by copper sulfate (1M, 0.27 mL, 0.274 mmol) were added. The reaction mixture was stirred at room temperature for 3 hours. The gummy solid formed was dissolved in a minimum of DCM and the mixture was pour into ethyl acetate (150 mL). The organic layer was washed with water (2 times) and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography (100% ethyl acetate) to afford title compound 450 (160 mg, 31%) as a colorless oil. MS (m/z): 379.3 (M+H).

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at room temperature for 3 hours
  3. customThe gummy solid formed
  4. washThe organic layer was washed with water (2 times) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-635471c89d12466581c2da4cebd8ba29
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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