HCID 57423706, compound → HCID 57423708, compound

HRID 1725171Notes

Reaction equation

HRID 1725171 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(C)(C)C>FC(F)(F)C(O)=O>[C:19]([C:9]1[N:8]([CH2:7][C:6]([OH:27])=[O:5])[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 57423706HCID 57423706, compound

Product 1

HCID 57423708HCID 57423708, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl(2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetate (148 mg, 0.41 mmol) in trifluoroacetic acid was stirred for 2 h at room temperature. After removal of trifluoroacetic acid, the residue was treated with CH2Cl2 (10 ml), MeOH (1 ml) and H2O (10 ml). The two layers were separated and the aqueous was extracted with CH2Cl2 (3×10 ml). The combined organic extracts were washed with H2O (10 ml), brine (10 ml), dried (Na2SO4) filtered and concentrated. The crude material was purified by chromatography (silica gel, EtOAc/hexane/HCO2H: 10/40/0.1) to afford (2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetic acid (125 mg, 100%) as an oil. To a stirred solution of (2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetic acid (260 mg, 0.85 mmol) in DMF (2.0 ml) was added 1,1′-carbonyldiimidazole (166 mg, 1.02 mmol) at room temperature. After stirring for 1 h, the reaction mixture was treated with a solution of guanidine hydrochloride (244 mg, 2.55 mmol) in DMF (2.5 ml) and triethylamine (0.54 ml, 2.55 mmol). After stirring over night, the reaction mixture was quenched with H2O (30 ml). The aqueous was extracted with Et2O (3×30 ml), EtOAc (10 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude material was purified by chromatography (silica gel; EtOAc/hexane/2M NH3 in MeOH: 65/35/1) to give the titled compound (169 mg, 58%) as a white solid: mp 201-203° C.; MS (−) ES, 345 (M−H)−.

Workup

  1. customAfter removal of trifluoroacetic acid
  2. additionthe residue was treated with CH2Cl2 (10 ml), MeOH (1 ml) and H2O (10 ml)
  3. customThe two layers were separated
  4. extractionthe aqueous was extracted with CH2Cl2 (3×10 ml)
  5. washThe combined organic extracts were washed with H2O (10 ml), brine (10 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography (silica gel, EtOAc/hexane/HCO2H: 10/40/0.1)

Sources & evidence

ORD record
ord-b28d6efb9d954298a9aac6d5b5441b25
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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