Phosphoric Acid → HCID 67340740, compound

HRID 334343Notes

Reaction equation

HRID 334343 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH2:28][CH3:29])=[C:22]([O:25][CH3:26])[CH:23]=3)[C@@H:18]3[C@@H:13]([CH2:14][CH2:15][C@@H:16]([OH:30])[CH2:17]3)[N:12]=2)=[CH:7][N:6]=1)=N.O[Li].O.P(=O)(O)(O)[OH:35].P([O-])([O-])(O)=O.[Na+].[Na+]>C1COCC1>[CH2:28]([O:27][C:21]1[CH:20]=[C:19]2[C:24]([C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:2])=[O:35])=[N:6][CH:7]=3)=[N:12][C@H:13]3[C@@H:18]2[CH2:17][C@H:16]([OH:30])[CH2:15][CH2:14]3)=[CH:23][C:22]=1[O:25][CH3:26])[CH3:29]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 24203Sodium Phosphate, DibasicHCID 168937Lithium hydroxide, monohydrateHCID 67341286HCID 67341286, compound

Product 1

HCID 67340740HCID 67340740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a second step, 443 mg (1.08 mmol) of 5-((2R,4aR,10bR)-9-ethoxy-2-hydroxy-8-methoxy-1,2,3,4,4a,10b-hexahydro-phenanthridin-6-yl)-pyridine-2-carboximidic acid methyl ester are dissolved in 3 ml of THF. A solution of 51 mg (2.16 mmol) LiOH.H2O is added and the solution stirred at 60° C. for 18 hrs. The pH is adjusted to 5 using phosphoric acid and Disodiumhydrogenphosphate. The solvent is removed and the solid residue extracted with chloroform/methanol. After filtering off and removing the volatiles 350 mg (82%) of the title compound are obtained.

Workup

  1. customThe solvent is removed
  2. extractionthe solid residue extracted with chloroform/methanol
  3. filtrationAfter filtering off
  4. customremoving the volatiles 350 mg (82%) of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-d912765d06e140528287e489e7182fc7
Source dataset
uspto-grants-2014_11
Patent number
US08883818B2

Reaction notes

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