Carbon Tetrachloride → 2-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine-N-methyl amide

HRID 276117

Reaction equation

HRID 276117 reaction equation
[CH3:1][NH:2][C:3](=[O:41])[C@H:4]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:8][C:9](=[O:24])[CH:10]([S:14]CC1C=CC(OC)=CC=1)[CH2:11][CH2:12][CH3:13].C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:1][NH:2][C:3](=[O:41])[C@H:4]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[NH:5][C:6](=[O:33])[C@H:7]([CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:8][C:9](=[O:24])[CH:10]([SH:14])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 867578252-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide

Product 1

HCID 598787442-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine-N-methyl amideYield 80.5%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide (0.26 g, 0.45 mmol), mercury (II) acetate (0.156 g, 0.49 mmol), and anisole (0.49 mL, 4.5 mmol) in dichloromethane (10 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen. Add trifluoroacetic acid (2 mL). After 3 hours, filter and evaporate in vacuo to give a residue. Repeatedly, combine the residue and carbon tetrachloride and evaporate in vacuo to give a residue. Triturate the residue with hexane to give the title compound as a solid (165 mg, 80.4%).

Workup

  1. temperatureCool in an ice bath
  2. customdegas
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue
  6. customevaporate in vacuo
  7. customto give a residue
  8. customTriturate the residue with hexane

Sources & evidence

ORD record
ord-27473199c8ff43b1ac82c772cd020e0b
Source dataset
uspto-grants-2002_03
Patent number
US06352976B1

Linked notes

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