Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate

HRID 1880491Notes

Reaction equation

HRID 1880491 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:25][C@H:24]([C:23]([O:22][CH3:21])=[O:30])[CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2723695Leucine methyl ester hydrochlorideHCID 21262853(4-Bromophenyl)(4-(methylsulfonyl)phenyl)methanone

Product 1

HCID 86590539methyl N-{(4-bromophenyl)[4-(methylsulfonyl)phenyl]methylene}leucinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (4-bromophenyl)[4-(methylsulfonyl)phenyl]methanone (202 mg, 0.59 mmol), L-leucine methyl ester hydrochloride (328 mg, 2.0 mmol) and camphor sulfonic acid (52 mg, 0.22 mmol) in toluene was refluxed for 18 hours using a Dean-Stark trap. The solvent was removed in vacuo and the resulting residue was purified by chromatography using EtOAc and hexane as eluant to give a 1:1 mixture of the title compound and the starting (4-bromophenyl)[4-(methylsulfonyl)phenyl]methanone.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by chromatography
  3. customto give

Sources & evidence

ORD record
ord-b45d1c2a8f9e4a70988eb46248f12e82
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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