Hydrochloric Acid → HCID 178524079, compound

HRID 2225166Notes

Reaction equation

HRID 2225166 reaction equation
C([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)[CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[C:11]12([C:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[NH:7][N:8]=3)[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:19]3)[CH2:18]1)[CH2:20]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178468570HCID 178468570, compound

Product 1

HCID 178524079HCID 178524079, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation C13, Step 3: 5-Adamantan-1-yl-2H-pyrazole-3-carboxylic acid ethyl ester (1.00 g, 3.64 mmol, 1 eq.) was dissolved in THF (20 mL) at RT then 1.000 N NaOH (7.29 mL, 7.29 mmol, 2 eq.) was added. Stirred overnight. Stripped off the THF in vacuo then adjusted the pH=3 with 1 N HCl. Extracted 3 times with ethyl acetate (25 mL). The organic layers were combined, dried and stripped to give 830 mg of 5-adamantan-1-yl-2H-pyrazole-3-carboxylic acid as an off-white solid. MS found: (M+H)+=247.

Workup

  1. customPreparation C13, Step 3
  2. extractionExtracted 3 times with ethyl acetate (25 mL)
  3. customdried

Sources & evidence

ORD record
ord-882fb42f097d4acfb4a30dec6a500abc
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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