1,2-Dichloroethane → HCID 66629560, compound

HRID 882344Notes

Reaction equation

HRID 882344 reaction equation
C(Cl)CCl.[C:5](=[N:8][OH:9])([NH2:7])[CH3:6].[C:10]([O:14][C:15]([N:17]([C@@H:22]1[CH2:24][C@H:23]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][C:19](O)=O)=[O:16])([CH3:13])([CH3:12])[CH3:11]>COCCOCCOC>[CH3:6][C:5]1[N:7]=[C:19]([CH2:18][N:17]([C@H:22]2[CH2:24][C@H:23]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:15](=[O:16])[O:14][C:10]([CH3:13])([CH3:11])[CH3:12])[O:9][N:8]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 30926N-HydroxyacetamidineHCID 66629327HCID 66629327, compound

Product 1

HCID 66629560HCID 66629560, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
50 °C

Procedure

EDC (107 μL, 0.585 mmol) and acetoamidoxime (41 mg, 0.532 mmol) was added to a stirred solution of 2-(tert-butoxycarbonyl((trans)-2-phenylcyclopropyl)amino)acetic acid (163 mg, 0.532 mmol) in diglyme (2 mL) under argon atmosphere. The mixture was stirred at 50° C. overnight and then at 110° C. for 14 hours. After removal of solvent under vacuum, the reaction mixture was purified by flash chromatography eluting with hexane/MTBE (80:20 to 0:100) to afford tert-butyl (3-methyl-1,2,4-oxadiazol-5-yl)methyl((1S,2S)-2-phenylcyclopropyl)carbamate as a colourless oil (35 mg. Yield=20%).

Workup

  1. waitat 110° C. for 14 hours
  2. customAfter removal of solvent under vacuum
  3. customthe reaction mixture was purified by flash chromatography
  4. washeluting with hexane/MTBE (80:20 to 0:100)

Sources & evidence

ORD record
ord-eb6e470e1a4742ed950b740749780584
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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