Anisole → N,N'-di-(4-chlorophenethyl)-2-(2-mercapto-3-phenylpropionylamino)malonamide

HRID 2269826Notes

Reaction equation

HRID 2269826 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:44])[CH:10]([NH:23][C:24](=[O:43])[C@@H:25]([S:33]CC2C=CC(OC)=CC=2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[O:12])=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:44])[CH:10]([NH:23][C:24](=[O:43])[CH:25]([SH:33])[CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 20713101N,N'-di-(4-chlorophenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide

Product 1

HCID 18348091N,N'-di-(4-chlorophenethyl)-2-(2-mercapto-3-phenylpropionylamino)malonamideYield 80%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine of N,N′-di-(4-chlorophenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide (0.29 g, 0.43 mmol), mercury (II) acetate (0.171 g, 0.54 mmol), and anisole (0.47 mL) in dichloromethane (10 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add trifluoroacetic acid (4 mL). After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. Filter and evaporate in vacuo to give a residue. Triturate the residue with diethyl ether to give the title compound as a solid (80%).

Workup

  1. temperatureCool in an ice bath
  2. customdegas
  3. custompurge with hydrogen sulfide (gas) for about 10 minutes
  4. filtrationFilter
  5. customevaporate in vacuo
  6. customto give a residue
  7. customTriturate the residue with diethyl ether

Sources & evidence

ORD record
ord-29e1b160da1e45e6972254ea4e4f50a5
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

Loading…