Sodium Hydroxide → HCID 68954276, compound

HRID 1453840Notes

Reaction equation

HRID 1453840 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:25]([O:27][CH3:28])=[O:26])=[N:11][N:12]2[CH:17]([C:18]([O:20]CC)=[O:19])[CH2:16][N:15]([CH3:23])[C:14](=[O:24])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([C:25]([O:27][CH3:28])=[O:26])=[N:11][N:12]2[CH:17]([C:18]([OH:20])=[O:19])[CH2:16][N:15]([CH3:23])[C:14](=[O:24])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68951392Methyl 3-benzyloxy-7-ethoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Product 1

HCID 68954276HCID 68954276, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3-benzyloxy-7-ethoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate (195 mg, 0.503 mmol) in MeOH/THF (0.5 mL) was added aqueous 1N NaOH (554 μL, 0.554 mmol). The mixture was stirred for 1 hour and quenched by the addition aqueous 3N HCl (170 μL). Purification by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions afforded the title product as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 7.49-7.47 (m, 2H), 7.40-7.33 (m, 3H), 5.44 (br s, 1H), 5.21 (dd, J=11.2, 30.4 Hz, 2H), 4.18 (dd, J=4.8, 13.6 Hz, 1H), 3.91 (d, J=13.6 Hz, 1H), 3.80 (s, 3H), 3.01 (s, 3H); ES MS (M+H)=360.

Workup

  1. customquenched by the addition aqueous 3N HCl (170 μL)
  2. customPurification by reverse phase chromatography on a C-18 column
  3. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA) and collection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-34ee6c839baa43528fb84a0d390ad7b4
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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