m-Chloroperbenzoic acid → HCID 66727336, compound

HRID 1845962Notes

Reaction equation

HRID 1845962 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[N:23][CH:22]=[CH:21]3)(=[O:17])=[O:16])[C@@H:10]([CH3:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[N+:23]([O-:37])[CH:22]=[CH:21]3)(=[O:16])=[O:17])[C@@H:10]([CH3:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66727237HCID 66727237, compound

Product 1

HCID 66727336HCID 66727336, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

340 mg of (S)-6-(4-tert-butoxycarbonyl-2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline was dissolved in 20 mL of dichloromethane, and 244 mg of m-chloroperbenzoic acid was added at 0° C. The reaction solution was stirred at room temperature for 16 hours and then concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:methanol=8:1) to obtain 320 mg of the compound of interest as a colorless oil (91%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe obtained crude product
  3. customwas purified by silica gel column chromatography (ethyl acetate:methanol=8:1)

Sources & evidence

ORD record
ord-33f5bbe581b749639b1c8dff372f5654
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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