Water → HCID 57528498, compound

HRID 1453821Notes

Reaction equation

HRID 1453821 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]([C:11](OC)=[O:12])=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]([C:23]([O:25][CH3:26])=[O:24])=[N:7]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>CN(C=O)C>[CH2:16]([O:15][C:9]1[C:8]([C:23]([O:25][CH3:26])=[O:24])=[N:7][N:6]2[CH2:5][CH2:4][NH:1][C:11](=[O:12])[C:10]=12)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57528490Dimethyl 1-(2-azidoethyl)-4-benzyloxy-1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 57528498HCID 57528498, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of dimethyl 1-(2-azidoethyl)-4-benzyloxy-1H-pyrazole-3,5-dicarboxylate (0.84 g, 2.34 mmol) in anhydrous DMF at 0° C. was added triphenylphosphine (0.92 g, 3.50 mmol). Water (300 μL) was added and the reaction was heated to 90° C. for 3 days. The solvent was removed in vacuo, and the resulting white solid was purified by flash chromatography on silica gel using 0-10% MeOH/CHCl3 gradient elution. Collection and concentration of the appropriate fractions afforded an oily solid which was triturated with methanol to yield a white precipitate. The solid was collected by vacuum filtration to afford the title product. ES MS (M+1)=302.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting white solid was purified by flash chromatography on silica gel using 0-10% MeOH/CHCl3 gradient elution
  3. customCollection and concentration of the appropriate fractions
  4. customafforded an oily solid which
  5. customwas triturated with methanol
  6. customto yield a white precipitate
  7. filtrationThe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-fb80a56b6e1e438782ad9decf278b568
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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