m-Chloroperbenzoic acid → HCID 86605394, compound

HRID 1180427Notes

Reaction equation

HRID 1180427 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@H:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].ClC1C=C(C=CC=1)C(OO)=[O:37]>ClCCl>[C:1]([CH2:3][NH:4][C:5](=[O:31])[C@@H:6]([O:11][C@@H:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N+:21]([O-:37])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86605392HCID 86605392, compound

Product 1

HCID 86605394HCID 86605394, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-phenyl(4-pyridin-3-ylphenyl)methyl]oxy}pentanamide from example 38 (95 mg, 0.23 mmol) in dichloromethane (10 mL) was added 77% quality 3-chloroperoxybenzoic acid (51.5 mg, 0.23 mmol) at 5° C. The temperature was permitted to gradually rise to r.t. over 1.5 h. The mixture was concentrated and the residue partitioned between ethyl acetate and 1M Na2CO3. The ethyl acetate layer was dried (Na2SO4) and concentrated to yield 100 mg of the title compound. Purification by chromatography on silica gel using 10% methanol in dichloromethane and concentrating with diethyl ether 2 times gave a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and 1M Na2CO3
  3. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c5aebbd7014442929a2d9baa1d4c3fe5
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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