Sodium Hydroxide → HCID 59900557, compound

HRID 2228785Notes

Reaction equation

HRID 2228785 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:14]=[C:15]([CH:39]=[CH:40][CH:41]=1)[CH2:16][CH2:17][NH:18][C:19]1[C:20](=[O:38])[N:21]([CH2:27][C:28]([O:30]CC2C=CC=CC=2)=[O:29])[C:22]([CH3:26])=[C:23](Cl)[N:24]=1)[CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].[OH-].[Na+]>[Pd].CO>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:14]=[C:15]([CH:39]=[CH:40][CH:41]=1)[CH2:16][CH2:17][NH:18][C:19]1[C:20](=[O:38])[N:21]([CH2:27][C:28]([OH:30])=[O:29])[C:22]([CH3:26])=[CH:23][N:24]=1)[CH2:10][O:11][CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 59900593HCID 59900593, compound

Product 1

HCID 59900557HCID 59900557, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-[3-[(3-{(1R/S)-1-[(tert-butoxycarbonyl)amino]-2-methoxyethyl}phenethyl)amino]-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate (preparation 122) (248 mg, 0.42 mmol), ammonium formate (265 mg, 4.2 mmol) and 10% palladium on charcoal (100 mg) in methanol (10 ml) was heated under reflux for 25 hrs. The cooled reaction was filtered through Arbocel®, and NaOH (420 ml, 10M, 4.2 mmol) was added to the filtrate. This mixture was evaporated under reduced pressure, triturated and filtered with a dichloromethane:methanol (91:9) solution (3×), and the combined filtrates evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0 to 93:7) to give the title compound as an oil, (35 mg, 18%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 25 hrs
  3. customThe cooled reaction
  4. additionwas added to the filtrate
  5. customThis mixture was evaporated under reduced pressure
  6. customtriturated
  7. filtrationfiltered with a dichloromethane:methanol (91:9) solution (3×)
  8. customthe combined filtrates evaporated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0 to 93:7)

Sources & evidence

ORD record
ord-e370b930bd9944f6805a68fd426d6b3d
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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