m-Chloroperbenzoic acid → HCID 86751075, compound

HRID 265349Notes

Reaction equation

HRID 265349 reaction equation
[Br:1][C@@H:2]1[C@H:9]([O:10][C:11](=[O:17])[NH:12][C:13](=[O:16])[CH2:14][Cl:15])[CH2:8][CH2:7][C@@:4]2([O:6][CH2:5]2)[C@@:3]1([OH:21])[C:18]([CH3:20])=[CH2:19].ClC1C=CC=C(C(OO)=[O:30])C=1.CCCCCC.C(OCC)(=O)C>ClCCl>[Br:1][C@@H:2]1[C@H:9]([O:10][C:11](=[O:17])[NH:12][C:13](=[O:16])[CH2:14][Cl:15])[CH2:8][CH2:7][C@@:4]2([O:6][CH2:5]2)[C@@:3]1([OH:21])[C:18]1([CH3:20])[CH2:19][O:30]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 86751076HCID 86751076, compound

Product 1

HCID 86751075HCID 86751075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By proceeding in accordance with the method of operation described in Example 2, starting from 2.14 g (5.6 mmol) of the crude compound obtained in Example 3 and 1.93 g (11.2 mmol) of 72% 3-chloroperbenzoic acid in 55 ml of dichloromethane, 0.9 g (2.26 mmol) of a mixture of the two expected diastereoisomers (73/27) is obtained in the form of a mousse after chromatography on silica gel twice (eluant: hexane/ethyl acetate, 3:1).

Sources & evidence

ORD record
ord-55e62b8b24c94c1da7be2e5d55ad708a
Source dataset
uspto-grants-1997_07
Patent number
US05648382

Reaction notes

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