Hydrochloric Acid → HCID 54092064, compound

HRID 378170Notes

Reaction equation

HRID 378170 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].NN=CNC1C=C(C(NCC([NH:24][CH:25]([C:30]2[CH:42]=[CH:41][C:40]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][C:32]=3[CH:31]=2)CC(O)=O)=O)=O)C=CC=1.Cl.[CH3:44][CH2:45]O>>[NH2:24][CH:25]([C:30]1[CH:42]=[CH:41][C:40]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:33][C:32]=2[CH:31]=1)[CH2:2][C:3]([O:5][CH2:44][CH3:45])=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178514383HCID 178514383, compound

Product 1

HCID 54092064HCID 54092064, compound

Procedure

The product from Step A was taken up in absolute EtOH, dry HCl gas was added to saturation, and the mixture refluxed overnight. Volatiles were removed and the resulting semi-solid partitioned between ethyl acetate and water. The aqueous layer was made basic by addition of 2.5N NaOH and extracted with EtOAc (2×200 mL). The organic layer was dried (anhydrous NaSO4) and dry HCl gas added until precipitation ceased. Volatiles were removed until a semisolid residue remained. This was triturated with diethyl ether to obtain a solid that was collected by filtration. NMR and MS were consistent with the proposed structure.

Workup

  1. temperaturethe mixture refluxed overnight
  2. customVolatiles were removed
  3. customthe resulting semi-solid partitioned between ethyl acetate and water
  4. additionThe aqueous layer was made basic by addition of 2.5N NaOH
  5. extractionextracted with EtOAc (2×200 mL)
  6. dry with materialThe organic layer was dried (anhydrous NaSO4) and dry HCl gas
  7. additionadded until precipitation
  8. customVolatiles were removed until a semisolid residue
  9. customThis was triturated with diethyl ether
  10. customto obtain a solid
  11. filtrationthat was collected by filtration

Sources & evidence

ORD record
ord-026d9a4b8fa348a6ab4457f916cdbc93
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

Loading…