m-Chloroperbenzoic acid → HCID 86605397, compound

HRID 1180430Notes

Reaction equation

HRID 1180430 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:35])[C@@H:6]([O:11][C@@H:12]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][O:33][CH3:34])[CH2:26]2)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].ClC1C=C(C=CC=1)C(OO)=[O:41].C([O-])(O)=O.[Na+]>ClCCl>[C:1]([CH2:3][NH:4][C:5](=[O:35])[C@@H:6]([O:11][C@@H:12]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][CH2:28][N+:27]([CH2:31][CH2:32][O:33][CH3:34])([O-:41])[CH2:26]2)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86605398HCID 86605398, compound

Product 1

HCID 86605397HCID 86605397, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-N-(cyanomethyl)-2-{[(R)-{4-[1-(2-methoxyethyl)piperidin-3-yl]phenyl}(phenyl)methyl]oxy}-4-pentanamide from example 41 step 3 (390 mg, 0.81 mmol) in dichloromethane (12 mL) at 0° C. was added 77% quality 3-chloroperoxybenzoic acid (183 mg, 0.81 mmol). The mixture was stirred for 5 minutes and then 5% NaHCO3 solution (10 mL) was added with stirring. The dichloromethane layer was separated, dried (Na2SO4), filtered and concentrated. The residue was chromatographed on silica gel using 30% methanol in ethyl acetate as eluent to obtain the title compound as a foam.

Workup

  1. stirringwith stirring
  2. customThe dichloromethane layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using 30% methanol in ethyl acetate as eluent

Sources & evidence

ORD record
ord-7d7e52d5414d43609638e14b11b2ead2
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

Loading…