m-Chloroperbenzoic acid → HCID 87338433, compound

HRID 468580Notes

Reaction equation

HRID 468580 reaction equation
[CH2:1]([N:26]1[C:30]([CH3:32])([CH3:31])[C:29](=[O:33])[N:28]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([C:42]([F:45])([F:44])[F:43])[CH:35]=2)[C:27]1=[O:46])/[CH:2]=[CH:3]\[CH2:4][N:5]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[N:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=2)[C:6]1=[O:25].C(Cl)Cl.CC[OH:52].ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[O:52]1[C@@H:2]([CH2:1][N:26]2[C:30]([CH3:32])([CH3:31])[C:29](=[O:33])[N:28]([C:34]3[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([C:42]([F:45])([F:44])[F:43])[CH:35]=3)[C:27]2=[O:46])[C@H:3]1[CH2:4][N:5]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[N:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:23])([F:24])[F:22])[CH:14]=2)[C:6]1=[O:25]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21584144Dichloromethane ethanolHCID 131731127HCID 131731127, compound

Product 1

HCID 87338433HCID 87338433, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 21 (90 mg, 0.139 mmol) is mixed under argon with 3-metachloroperbenzoic acid (72.5 mg, 0.210 mmol) in anhydrous dichloromethane (10 ml). The mixture is stirred at ambient temperature. The progression of the reaction is monitored by TLC (eluent DCM/EtOH: 95/05). After 4 days, starting compound remains. A fresh quantity of metachloroperbenzoic acid (0.124 g, 0.36 mmol) is added to the reaction medium and the reaction medium is stirred at ambient temperature for another 4 days. The solvent is evaporated off under reduced pressure and the residue is purified by flash chromatography (BIOTAGE 25+M column, gradient dichloromethane/acetone: 0% to 8% of acetone). The expected compound is obtained in the form of a white solid, with a yield of 50%. Melting point: 108-110° C.

Workup

  1. stirringthe reaction medium is stirred at ambient temperature for another 4 days
  2. customThe solvent is evaporated off under reduced pressure
  3. customthe residue is purified by flash chromatography (BIOTAGE 25+M column, gradient dichloromethane/acetone: 0% to 8% of acetone)

Sources & evidence

ORD record
ord-1dd77db520df49f997e76e83af1f02b7
Source dataset
uspto-grants-2014_01
Patent number
US08624037B2

Reaction notes

Loading…