Water → Methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate

HRID 1453866Notes

Reaction equation

HRID 1453866 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]([C:12](OC)=[O:13])=[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]([C:24]([O:26][CH3:27])=[O:25])=[N:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH2:17]([O:16][C:10]1[C:9]([C:24]([O:26][CH3:27])=[O:25])=[N:8][N:7]2[CH2:6][CH2:5][CH2:4][NH:1][C:12](=[O:13])[C:11]=12)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86617824HCID 86617824, compound

Product 1

HCID 68952653Methyl 3-benzyloxy-4-oxo-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 1-(3-azidopropyl)-4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (152 mg, 0.407 mmol) in THF (2 mL) were added triphenylphosphine (107 mg, 0.407 mmol) and water (37 μL, 2.036 mmol). The reaction was stirred at room temperature overnight, and the solvent was removed in vacuo. The residue was dissolved in toluene and heated to 110° C. overnight. 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. 1H NMR (400 MHz, CDCl3) δ 7.44-7.41 (m, 2H), 7.34-7.28 (m, 3H), 6.70 (br s, 1H), 5.29 (s, 2H), 4.46-4.42 (t, 2H), 3.96 (s, 3H), 3.06-3.00 (m, 2H), 2.20-2.13 (m, 2H); ES MS (M+1)=316.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in toluene
  3. temperatureheated to 110° C. overnight
  4. customPurification by reverse phase chromatography on a C-18 column
  5. 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-a9bc9b4c3103489dbe5559f35006fd05
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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