Hydrazine hydrate (1:1) → HCID 13670591, compound

HRID 414203Notes

Reaction equation

HRID 414203 reaction equation
Cl.[NH2:2][NH2:3].O.NN.C[O:8][C:9]([C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][C:18]=3[CH3:28])[N:13]([CH3:14])[CH2:12]1)=O>C(O)CC>[CH3:28][C:18]1[NH:19][C:20]2[C:27]3[C:17]=1[CH2:16][C@@H:15]1[C:25]([C:24]=3[CH:23]=[CH:22][CH:21]=2)=[CH:26][C@H:11]([C:9]([NH:2][NH2:3])=[O:8])[CH2:12][N:13]1[CH3:14]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 115031Hydrazinium chlorideHCID 54410625HCID 54410625, compound

Product 1

HCID 13670591HCID 13670591, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

15.9 g hydrazine hydrochloride and 18.4 ml hydrazine hydrate are added under stirring to 22.5 g of the product of step (a) in 20 ml n-propanol and the obtained reaction mixture is heated under reflux for 5 hours. The mixture is concentrated, treated with 500 ml H2O, filtered and washed with H2O (fraction A). The mother liquor is extracted with ethyl acetate and the extract evaporated. To the residue (7.5 g) are added 100 ml n-propanol and 20 ml triethylamine and the mixture is stirred and heated at reflux. The reaction is followed by thin layer chromatography. After approximately 15 hours when all of the β-product is converted into the 8α-product, H2O is added and the mixture is filtered. The filter cake is combined with fraction A and recrystallized twice from hot ethanol to afford the heading compound, m.p. 235°-240°, which is the pure α-isomer by NMR.

Workup

  1. customthe obtained reaction mixture
  2. temperatureis heated
  3. temperatureunder reflux for 5 hours
  4. concentrationThe mixture is concentrated
  5. additiontreated with 500 ml H2O
  6. filtrationfiltered
  7. washwashed with H2O (fraction A)
  8. extractionThe mother liquor is extracted with ethyl acetate
  9. customthe extract evaporated
  10. additionTo the residue (7.5 g) are added 100 ml n-propanol and 20 ml triethylamine
  11. temperatureheated
  12. temperatureat reflux
  13. additionis added
  14. filtrationthe mixture is filtered
  15. customrecrystallized twice from hot ethanol
  16. customto afford the heading compound, m.p. 235°-240°, which

Sources & evidence

ORD record
ord-a66c2d9c52ba4bfda73c5c6196343d47
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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