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Methyl Glycolate → {5-[1-(4-Cyano-3-fluorophenyl)-1-hydroxyethyl]imidazol-1-yl}acetic acid methyl ester

HRID 2306217
Notes
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Reaction equation

HRID 2306217 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:12]2[N:13]=[CH:14][N:15](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:16]=2)([OH:11])[CH3:10])=[CH:5][C:4]=1[F:36])#[N:2].[C:37]([O:41][CH3:42])(=[O:40])[CH2:38]O.C(N(CC)C(C)C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[CH3:42][O:41][C:37](=[O:40])[CH2:38][N:13]1[C:12]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:36])[CH:5]=2)([OH:11])[CH3:10])=[CH:16][N:15]=[CH:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 66774Methyl GlycolateHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 184336071-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

Product 1

HCID 53834038{5-[1-(4-Cyano-3-fluorophenyl)-1-hydroxyethyl]imidazol-1-yl}acetic acid methyl ester

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(4-cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol, as described above in Step C, (200 mg, 0.42 mmol), methyl glycolate (35 mg, 0.39 mmol), and N,N-diisopropylethylamine (65 mg, 0.51 mmol) in dry CH2Cl2 (10 mL), under argon, at −78° C., was added trifluoromethanesulfonic anhydride (110 mg, 0.39 mmol) dropwise. The mixture was allowed to warm slowly to ambient temperature, then the solvent was removed in vacuo. The residue was dissolved in MeOH (10 mL) and the solution was heated to reflux for 1 hour, then concentrated to dryness. The residue was purified by silica gel chromatography, eluting with 4% MeOH—0.4% NH4OH in CHCl3, to yield the titled product as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. temperaturethe solution was heated
  4. temperatureto reflux for 1 hour
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 4% MeOH—0.4% NH4OH in CHCl3

Sources & evidence

ORD record
ord-3235987975cd41b79c20e200728d3ab9
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06441017B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes