Sodium Hydroxide → HCID 18470961, compound

HRID 567857Notes

Reaction equation

HRID 567857 reaction equation
C([O-])=O.[NH4+].[C:5]([O:9][C:10]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:42]=[CH:43][CH:44]=1)[CH2:19][CH2:20][NH:21][C:22]1[C:23](=[O:41])[N:24]([CH2:30][C:31]([O:33]CC2C=CC=CC=2)=[O:32])[C:25]([CH3:29])=[C:26](Cl)[N:27]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[OH-].[Na+]>[Pd].CO>[C:5]([O:9][C:10]([NH:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:42]=[CH:43][CH:44]=1)[CH2:19][CH2:20][NH:21][C:22]1[C:23](=[O:41])[N:24]([CH2:30][C:31]([OH:33])=[O:32])[C:25]([CH3:29])=[CH:26][N:27]=1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 18470852HCID 18470852, compound

Product 1

HCID 18470961HCID 18470961, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on charcoal (125 mg), followed by ammonium formate (553 mg, 8.77 mmol) were added to a solution of benzyl 2-[3-{[3-({2-[(tert-butoxycarbonyl)amino]ethoxy})phenethyl]amino}-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 129) (500 mg, 0.88 mmol) in methanol (10 ml), and the reaction stirred at room temperature overnight. The reaction mixture was filtered through Whatman® fibre, NaOH solution (8.77 ml, 1N, 8.77 mmol) was added to the filtrate, and the solution evaporated under reduced pressure. The residue was triturated with a 10% methanol:dichloromethane solution, the suspension filtered, the filtrate dried over MgSO4 and evaporated under reduced pressure to give the title compound as a white solid, (289 mg, 69%).

Workup

  1. additionwas added to the filtrate
  2. customthe solution evaporated under reduced pressure
  3. customThe residue was triturated with a 10% methanol
  4. filtrationdichloromethane solution, the suspension filtered
  5. dry with materialthe filtrate dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3c833461a8c24e2987e53a16bd0ba34a
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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