Sodium Hydroxide → HCID 178452921, compound

HRID 1946272Notes

Reaction equation

HRID 1946272 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][NH:7][N:6]=1)=[O:4].[OH-].[Na+].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>O1CCOCC1>[C:17]([O:16][C:14]([NH:10][C:9]1[C:5]([C:3]([OH:2])=[O:4])=[N:6][NH:7][CH:8]=1)=[O:13])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 178499176HCID 178499176, compound

Product 1

HCID 178452921HCID 178452921, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-amino-1H-pyrazole-3-carboxylic acid methyl ester (50.0 g, 355 mmol) in dioxane (500 mL) was added 2M aqueous NaOH solution (213 mL, 426 mmol), the mixture heated to 50° C. and stirred for 5 h. To this mixture was then added (BOC)2O (81.4 g, 373 mmol), using a dioxane rinse (100 mL) and the mixture heated at 50° C. for a further 5 h, then stirred at ambient for 14 h. The dioxane was removed in vacuo and water (1 L) added. The mixture was taken to pH 2 using conc. aqueous HCl solution and the solid formed collected by filtration and dried on the filter. The solid was dried further through azeotrope with toluene (x3) and in the vacuum oven to give 4-tert-butoxycarbonylamino-1H-pyrazole-3-carboxylic acid (70.0 g, 87%) as a violet solid.

Workup

  1. washrinse (100 mL)
  2. temperaturethe mixture heated at 50° C. for a further 5 h
  3. stirringstirred at ambient for 14 h
  4. customThe dioxane was removed in vacuo and water (1 L)
  5. additionadded
  6. customthe solid formed
  7. filtrationcollected by filtration
  8. customdried on the filter
  9. dry with materialThe solid was dried further through azeotrope with toluene (x3) and in the vacuum oven

Sources & evidence

ORD record
ord-ab12a30072a742f682501cac017f9175
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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