Veratrole → N,N'-di-(3,4-dimethoxyphenethyl)-2-((S)-2-mercapto-3-phenylpropionylamino)malonamide

HRID 2269830Notes

Reaction equation

HRID 2269830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:48]=[CH:49][C:50]=1[O:51][CH3:52])[CH2:6][CH2:7][NH:8][C:9](=[O:47])[CH:10]([NH:26][C:27](=[O:46])[C@@H:28]([S:36]CC1C=CC(OC)=CC=1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[O:12].C1(OC)C=CC=CC=1.C1(OC)C(=CC=CC=1)OC.ClCCl.C(OCC)(=O)C.CCCCCC>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C.ClCCl.C(OCC)(=O)C>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[O:22][CH3:23])[CH2:15][CH2:14][NH:13][C:11](=[O:12])[CH:10]([NH:26][C:27](=[O:46])[C@@H:28]([SH:36])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:9]([NH:8][CH2:7][CH2:6][C:5]1[CH:48]=[CH:49][C:50]([O:51][CH3:52])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:47]

Participants

8

Reactant 4

HCID 7043VeratroleHCID 7519AnisoleHCID 20713096N,N'-di-(3,4-dimethoxyphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamideHCID 21942482Ethyl acetate hexane methylene-chloride

Product 1

HCID 9851856N,N'-di-(3,4-dimethoxyphenethyl)-2-((S)-2-mercapto-3-phenylpropionylamino)malonamide

Reagents, catalysts & solvents 3

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Combine of N,N′-di-(3,4-dimethoxyphenethyl)-2-((S)-2-(p-methoxybenzylmercapto)-3-phenylpropionylamino)malonamide (0.139 g, 0.19 mmol), mercury (II) acetate (0.076 g), and anisole (0.3 mL), and veratrole (0.24 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. Chromatograph the residue on silica gel eluting with 3/1 dichloromethane/ethyl acetate/hexane and then 3/2 dichloromethane/ethyl acetate to give the title compound.

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

Sources & evidence

ORD record
ord-af53cadabd0d48f68ef9d1e5e15c375d
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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