m-Chloroperbenzoic acid → HCID 86751073, compound

HRID 265348Notes

Reaction equation

HRID 265348 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C@@H:13]1[C@H:20]([O:21][C:22](=[O:28])[NH:23][C:24](=[O:27])[CH2:25][Cl:26])[CH2:19][CH2:18][C@@:15]2([O:17][CH2:16]2)[C@@:14]1([OH:33])[C:29]([CH3:32])=[CH:30][CH3:31]>ClCCl>[Br:12][C@@H:13]1[C@H:20]([O:21][C:22](=[O:28])[NH:23][C:24](=[O:27])[CH2:25][Cl:26])[CH2:19][CH2:18][C@@:15]2([O:17][CH2:16]2)[C@@:14]1([OH:33])[C:29]1([CH3:32])[CH:30]([CH3:31])[O:9]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86751074HCID 86751074, compound

Product 1

HCID 86751073HCID 86751073, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.12 g (4.74 mmol) of 72% 3-chloroperbenzoic acid are added to a solution of 0.46 g (1.16 mmol) of the compound obtained in Example 1 in 30 ml of dichloromethane. The reaction mixture is stirred at room temperature for 5 hours. The solid formed during the course of the reaction is filtered off. After conventional treatment of the organic phase and purification by chromatography on silica gel twice (eluant: hexane/ethyl acetate, 3:2), 0.146 mg (0.354 mmol) of the expected compound is obtained in the form of a mousse.

Workup

  1. customThe solid formed during the course of the reaction
  2. filtrationis filtered off
  3. customAfter conventional treatment of the organic phase and purification by chromatography on silica gel twice (eluant: hexane/ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-288273e2a6fc43cf8d9e80c77d2148b6
Source dataset
uspto-grants-1997_07
Patent number
US05648382

Reaction notes

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