Hydrochloric Acid → HCID 71656242, compound

HRID 517912Notes

Reaction equation

HRID 517912 reaction equation
[CH3:1][O:2][C:3]1([CH3:38])[C:8]2=[N:9][C:10]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)[N:12]=[C:7]2[N:6]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[CH2:5][CH2:4]1.OC1(C)C2=NC(C3C=CC(C)=CC=3)=C(C3C=CC(C)=CC=3)N=C2N(CCCCCCC(OCC)=O)CC1.[OH-].[Na+].C(OCC)(=O)C.Cl>C(O)C>[CH3:1][O:2][C:3]1([CH3:38])[C:8]2[C:7](=[N:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[C:10]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:9]=2)[N:6]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 131733357HCID 131733357, compound

Product 1

HCID 71656242HCID 71656242, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the mixture of compounds from step 1 (120 mg) in Ethanol (5 ml) was added 2M NaOH (aq) (0.478 ml, 0.956 mmol) and the suspension was stirred under an atmosphere of nitrogen at room temperature overnight. The resulting suspension was treated ethyl acetate (20 ml) followed by 2M HCl (aq) (˜3 ml) until pH 5-6 was reached. The resulting mixture was washed with water (˜20 ml). The organic layer was separated and dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow oil/solid. Purification of the solid by chromatography on silica eluting with EtOAc in iso-hexane afforded the titled compound;

Workup

  1. washThe resulting mixture was washed with water (˜20 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow oil/solid
  7. customPurification of the solid by chromatography on silica eluting with EtOAc in iso-hexane

Sources & evidence

ORD record
ord-d25e29c9d0764a32a2f2ffd0e89a2665
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

Loading…