m-Chloroperbenzoic acid → HCID 69312791, compound

HRID 1392405Notes

Reaction equation

HRID 1392405 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3C=O)[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].ClC1C=CC=C(C(OO)=[O:45])C=1>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([C:19]([NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:45])[CH2:24][CH:23]2[OH:36])=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86601115HCID 86601115, compound

Product 1

HCID 69312791HCID 69312791, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(2-formylphenyl)piperidin-3-ol (1.38 g, 2.8 mmol) obtained in Step 1 of Example 61 in 50 ml of chloroform, was added 486 mg of m-chloroperbenzoic acid (5.6 mmol). The reaction mixture was stirred for about 2 hours at room temperature. The resulting organic layer was washed with the solutions of sulfurous acid and sodium bicarbonate, dried on sodium sulfate. The resulting ester residue was dissolved in 100 ml of methanol and was added a drop of concentrated hydrochloride thereto. The reaction mixture was stirred for about 1 hour, was added sodium bicarbonate (0.5 g) thereto. The reaction mixture was concentrated. The resulting residue was purified with column chromatography to give 1.0 g of the titled compound.

Workup

  1. washThe resulting organic layer was washed with the solutions of sulfurous acid and sodium bicarbonate
  2. customdried on sodium sulfate
  3. dissolutionThe resulting ester residue was dissolved in 100 ml of methanol
  4. additionwas added a drop of concentrated hydrochloride
  5. stirringThe reaction mixture was stirred for about 1 hour
  6. additionwas added sodium bicarbonate (0.5 g)
  7. concentrationThe reaction mixture was concentrated
  8. customThe resulting residue was purified with column chromatography

Sources & evidence

ORD record
ord-4236a3b3d7cd4a4891ebd29278c8dc5a
Source dataset
uspto-grants-2008_03
Patent number
US07342027B2

Reaction notes

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