Hydrochloric Acid → 3-Benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylic acid

HRID 1453867Notes

Reaction equation

HRID 1453867 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:20]([O:22]C)=[O:21])=[N:11][N:12]2[CH2:18][CH2:17][CH2:16][NH:15][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[CH2:18][CH2:17][CH2:16][NH:15][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 Hydroxide2×HCID 68952653Methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate

Product 1

HCID 689526853-Benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate (50 mg, 0.159 mmol) in MeOH (2 mL) was added aqueous 1M NaOH (159 μL, 0.159 mmol). The reaction was stirred at room temperature for 4 hours, treated with additional aqueous 1N NaOH (159 μL, 0.159 mmol), and stirred at room temperature overnight. Aqueous 1N HCl (318 μL, 0.318 mmol) was added to the solution, and the solvents were removed in vacuo to afford the title product. 1H NMR (400 MHz, CD3OD) δ 7.39-7.36 (m, 2H), 7.32-7.28 (m, 3H), 5.24 (s, 3H), 4.38-4.34 (t, 2H), 2.90-2.86 (t, 2H), 2.13-2.06 (dt, 2H); ES MS (M+1)=302.

Workup

  1. stirringstirred at room temperature overnight
  2. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-cb260ec7960746afadfbe1059bc3d7d3
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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