Sodium Carbonate → HCID 72714886, compound

HRID 571725Notes

Reaction equation

HRID 571725 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH2:7]([O:14][C:15]1[CH:19]=[C:18]([C:20](OCC)=[O:21])[N:17]([CH2:25][CH2:26][CH2:27][NH2:28])[N:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH2:7]([O:14][C:15]1[CH:19]=[C:18]2[C:20](=[O:21])[NH:28][CH2:27][CH2:26][CH2:25][N:17]2[N:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86706490HCID 86706490, compound

Product 1

HCID 72714886HCID 72714886, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Na2CO3 (25 g, 235.85 mmol) was added to a solution of ethyl 3-(benzyloxy)-1-[3-amino-propyl]-1H-pyrazole-5-carboxylate (5.5 g, 16.2 mmol) in water (150 mL). The mixture was stirred at room temperature for 18 hours and then extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in petroleum ether 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-(benzyloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (4 g, 73% yield).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in petroleum ether 0/100 to 50/50)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-8f9f7c80ac1342cd8d1e4f87bb5b1434
Source dataset
uspto-grants-2015_05
Patent number
US09029366B2

Reaction notes

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