Phosphate → HCID 66699126, compound

HRID 1095932Notes

Reaction equation

HRID 1095932 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]1[CH:9]=[C:8]([C:10](C)(C)[O:11][SiH2]C(C)(C)C)[CH:7]=[N:6]1.P([O-])([O-])([O-])=O>CC#N>[CH3:1][O:2][C:3](=[O:19])[CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[N:6]1

Participants

4

Reactant 2

HCID 1061PhosphateHCID 131729527HCID 131729527, compound

Product 1

HCID 66699126HCID 66699126, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrazol-1-yl]-acetic acid methyl ester (539 mg) was dissolved in CH3CN (8 mL) followed by the addition of aqueous HF solution (47-51%, 0.33 ml). Stirring was continued for 2 hours at r.t. The reaction mixture was poured into phosphate buffer solution (pH 7.0) and extracted with chloroform. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate) to give the title compound as a colorless oil (229 mg, 67%). MS (m/e)=171.2 [MH+].

Workup

  1. extractionextracted with chloroform
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-64273437fd054ae28fd1c22c1a86b266
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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