Potassium Carbonate → HCID 13670594, compound

HRID 414204Notes

Reaction equation

HRID 414204 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][C:6]1[NH:24][C:23]2[C:25]3[C:7]=1[CH2:8][C@@H:9]1[C:18]([C:19]=3[CH:20]=[CH:21][CH:22]=2)=[CH:17][C@H:12](C(NN)=O)[CH2:11][N:10]1[CH3:26].C([O-])([O-])=O.[K+].[K+]>O.Cl>[NH2:1][C@H:12]1[CH:17]=[C:18]2[C@@H:9]([CH2:8][C:7]3[C:25]4[C:23](=[CH:22][CH:21]=[CH:20][C:19]2=4)[NH:24][C:6]=3[CH3:5])[N:10]([CH3:26])[CH2:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13670591HCID 13670591, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13670594HCID 13670594, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

1.4 g sodium nitrite in 5 ml H2O are added dropwise within 10 minutes under ice-cooling and stirring to 6.8 g of the product of step (b) in 200 ml 0.2N HCl. The reaction mixture is stirred under ice-cooling for 15 minutes and added dropwise unter nitrogen to 100 ml refluxing 0.4N HCl within 15 minutes. Stirring is continued for 10 minutes. The mixture is then cooled, rendered alkaline with saturated K2CO3 solution and extracted about 7 times with 9:1 CH2Cl2 /l CH3OH, whereby the black residue remains in the aqueous phase. The organic phase is dried (Na2SO4), evaporated, the resulting foam is chromatographed on silica gel using 80:20:0.7 CH2Cl2 /CH3OH/NH3 to afford the heading compound as a brown resin (pure 8α-compound by NMR).

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 minutes
  3. additionadded dropwise unter nitrogen to 100 ml
  4. stirringStirring
  5. temperatureThe mixture is then cooled
  6. extractionextracted about 7 times with 9:1 CH2Cl2 /l CH3OH, whereby the black residue
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customevaporated
  9. customthe resulting foam is chromatographed on silica gel using 80:20:0.7 CH2Cl2 /CH3OH/NH3
  10. customto afford the heading compound as a brown resin (pure 8α-compound by NMR)

Sources & evidence

ORD record
ord-33c38a068b8345a191272f442586964a
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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