HCID 118223432, compound → HCID 118223433, compound

HRID 2200102Notes

Reaction equation

HRID 2200102 reaction equation
C1(C([N:6]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=3)[CH:17]=[CH:16][N:15]=2)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=O)CC1>Cl.O1CCOCC1>[CH3:27][C:26]1[C:21]([O:20][C:18]2[CH:17]=[CH:16][N:15]=[C:14]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH:19]=2)=[N:22][CH:23]=[C:24]([N+:28]([O-:30])=[O:29])[CH:25]=1

Participants

4

Reactant 1

HCID 118223432HCID 118223432, compound

Product 1

HCID 118223433HCID 118223433, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve the crude product obtained in Step 3 (2.14 g, 4.7 mmol) in HCl solution in 1,4-dioxane (5 M, 10 mL). Stir the reaction at room temperature for 17 hrs. LC/MS shows reaction is complete. Remove the solvent under reduced pressure, suspend the solid in DCM and add carefully saturated NaHCO3 solution. Separate the organic layer. Extract the aqueous layer with DCM. Combine the organic layers, dry over anhydrous Na2SO4. Concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:3) affords the title compound (0.9 g, 54% from step 2). MS: (M+1): 352.

Workup

  1. customthe reaction at room temperature for 17 hrs
  2. customreaction
  3. customRemove the solvent under reduced pressure
  4. additionadd carefully saturated NaHCO3 solution
  5. customSeparate the organic layer
  6. extractionExtract the aqueous layer with DCM
  7. dry with materialdry over anhydrous Na2SO4
  8. concentrationConcentrate
  9. customto give the crude product
  10. customPurification by chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-f1771ed54bc843f3989dc7b05e998207
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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