Trifluoromethanesulfonic anhydride → HCID 21193368, compound

HRID 443304Notes

Reaction equation

HRID 443304 reaction equation
C([N:20]1[CH:24]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(C(C)C)C(C)C.[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53]([CH2:56]O)[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53]([CH2:56][N:22]2[C:23]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=3)=[CH:24][N:20]=[CH:21]2)[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

Product 1

HCID 21193368HCID 21193368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-trityl-4-(4-Cyanobenzyl)-imidazole (1.99 g, 4.64 mmol) in CH2Cl2 (9.3 mL), Hunigs base (1.62 mL, 9.28 mmol) and the product from step B (1.0 g 4.64 mmol) at -78° C. was added trifluoromethanesulfonic anhydride (0.78 mL, 4.64 mmol). After 45minutes the reaction was allowed to warm to room temperature. The solvent was evaporated and the residue was dissolved in methanol (50 ml) and heated at reflux for 1 hour, cooled and evaporated to dryness. The residue was partitioned between sat. aq. NaHCO3 solution and CH2Cl2. The organic layer was dried, (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 3% MeOH in CH2Cl2) to afford the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methanol (50 ml)
  3. temperatureheated
  4. temperatureat reflux for 1 hour
  5. temperaturecooled
  6. customevaporated to dryness
  7. customThe residue was partitioned between sat. aq. NaHCO3 solution and CH2Cl2
  8. customThe organic layer was dried
  9. custom(MgSO4) and the solvent evaporated in vacuo
  10. customThe residue was chromatographed (Silica gel, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-37662f924c164feca8e259425f16217f
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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