HCID 178512352, compound → HCID 178512351, compound

HRID 378152Notes

Reaction equation

HRID 378152 reaction equation
[C:1]([N:3]=[C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]([NH:15][CH2:16][C:17]([NH:19][CH:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:21][C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[O:18])=[O:14])[CH:10]=[CH:11][CH:12]=1)[NH2:5])#[N:2]>CO.C1COCC1.[OH-].[Na+]>[NH2:5][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]([NH:15][CH2:16][C:17]([NH:19][CH:20]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:21][C:22]([OH:24])=[O:23])=[O:18])=[O:14])[CH:10]=[CH:11][CH:12]=1)=[N:3][C:1]#[N:2]

Participants

5

Reactant 1

HCID 178512352HCID 178512352, compound

Product 1

HCID 178512351HCID 178512351, compoundYield 27.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of the compound from Example 134 (285 mg) in methanol (3 ml) and THF (3 ml), 1N sodium hydroxide (3 ml) was added. The reaction mixture was stirred at room temperature for 2 hours, evaporated and the residue dissolved in water. The resulting solution was adjusted to pH 4 with 1N hydrochloric acid and extracted with ethyl acetate/MeOH. The organic extracts were washed with water, dried (Na2SO4) and evaporated to afford an off white solid. The crude product was further purified by reverse phase HPLC on a C18 column (eluant:0.5% TFA-water/acetonitrile) and lyophilized to afford the title compound (65 mg) as a white solid.

Workup

  1. customevaporated
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with ethyl acetate/MeOH
  4. washThe organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto afford an off white solid
  8. customThe crude product was further purified by reverse phase HPLC on a C18 column (eluant:0.5% TFA-water/acetonitrile)

Sources & evidence

ORD record
ord-83360ab08abc41a3b61742839078d150
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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