Sodium Hydroxide → HCID 9867367, compound

HRID 481419Notes

Reaction equation

HRID 481419 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:31][CH2:32][CH2:33][CH3:34])[N:8]=[C:9]([CH2:27][CH2:28][CH2:29][CH3:30])[C:10]=1[CH2:11][C:12]1[S:13][C:14]([C:17]2([C:22]([O:24]CC)=[O:23])[CH2:21][CH:20]=[CH:19][CH2:18]2)=[CH:15][CH:16]=1)=[O:5])C.[OH-].[Na+]>CO>[CH2:31]([N:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH2:11][C:12]2[S:13][C:14]([C:17]3([C:22]([OH:24])=[O:23])[CH2:21][CH:20]=[CH:19][CH2:18]3)=[CH:15][CH:16]=2)[C:9]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:8]1)[CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67666850HCID 67666850, compound2×

Product 1

HCID 9867367HCID 9867367, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Step 2, above (86) (40 mg), was dissolved in 1.0 ml of methanol and an excess of 2N NaOH (0.5 ml) was added. The reaction mixture was stirred at room temperature for 5 hours, evaporated to dryness and the residue taken up into water. The aqueous solution was extracted with ethyl acetate to remove unreacted starting material, then was acidified with acetic acid and extracted again with ethyl acetate. The EtOAc extract was dried and concentrated using heptane to azeotrope off any residual acetic acid. The resulting solid was precipitated from EtOAc/hexanes, filtered and dried under vacuum to yield the title compound (87).

Workup

  1. customevaporated to dryness
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. customto remove unreacted
  4. extractionextracted again with ethyl acetate
  5. extractionThe EtOAc extract
  6. customwas dried
  7. concentrationconcentrated
  8. customThe resulting solid was precipitated from EtOAc/hexanes
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-4f0c1e822abf49ad87ce08d09bd616ad
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

Loading…