Hydrochloric Acid → HCID 131732110, compound

HRID 1396996Notes

Reaction equation

HRID 1396996 reaction equation
CC(OC([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH:10]=[N:9]1)=O)(C)C.[ClH:16].CCOCC>O1CCCC1>[ClH:16].[NH:8]1[C@H:12]([C:13]([OH:15])=[O:14])[CH2:11][CH:10]=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68287959(5S)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-4,5-dihydro-1H-pyrazole-5-carboxylic acid

Product 1

HCID 131732110HCID 131732110, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 2000 ml round bottom flask was added (5S)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-4,5-dihydro-1H-pyrazole-5-carboxylic acid (34 g, 159 mmol) in tetrahydrofuran (THF) (600 mL), followed by HCl (397 mL, 1587 mmol) (4 M in dioxane). The mixture was stirred at room temperature for 18 hours, and then ether (600 mL) was added. After stirring for 5 min, the mixture was allowed to stand for 10 min and then the organic solvents were decanted. The solid was collected by filtration and dried under high vacuum to provide (5S)-4,5-dihydro-1H-pyrazole-5-carboxylic acid, hydrochloride (22.4 g, 149 mmol, 94% yield) as a pale yellow solid. 1H NMR (400 MHz, METHANOL-d4): δ ppm 3.40-3.66 (m, 2H) 4.75-4.84 (m, 1H) 8.05-8.13 (m, 1H).

Workup

  1. stirringAfter stirring for 5 min
  2. waitto stand for 10 min
  3. customthe organic solvents were decanted
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-7d3e96d85fc640acb665364abfde2594
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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