Hydrochloric Acid → 3-Benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid

HRID 1453856Notes

Reaction equation

HRID 1453856 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22]C)=[O:21])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[C:10]([C:20]([OH:22])=[O:21])=[N:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68951321Methyl 3-benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 689513253-Benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-benzyloxy-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (221 mg, 0.701 mmol) in MeOH (5 mL) was added 1N aqueous NaOH (2 mL, 2 mmol). The reaction was stirred for several hours at room temperature and treated with 1N aqueous HCl (2 mL, 2 mmol). The solvents were removed in vacuo to afford the title product. 1H NMR (400 MHz, CD3OD) δ 7.51-7.49 (m, 2H), 7.54-7.26 (m, 3H), 5.26 (s, 2H), 4.39-4.36 (t, 2H), 3.82-3.72 (t, 2H), 3.12 (s, 3H); ES MS (M+1)=302.

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-4a89780e9f3c4d94a08bcf0932dbd25e
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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