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

HRID 276114

Reaction equation

HRID 276114 reaction equation
C([O:5][C:6](=[O:44])[C@H:7]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:8][C:9](=[O:36])[C@H:10]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:11][C:12](=[O:27])[CH:13]([S:17]CC1C=CC(OC)=CC=1)[CH2:14][CH2:15][CH3:16])(C)(C)C.C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[SH:17][CH:13]([CH2:14][CH2:15][CH3:16])[C:12]([NH:11][C@H:10]([C:9]([NH:8][C@H:7]([C:6]([OH:44])=[O:5])[CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:36])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 544815592-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester

Product 1

HCID 155487402-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanineYield 58.2%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester (0.20 g, 0.33 mmol), mercury (II) acetate (0.134 g, 0.42 mmol), and anisole (0.37 mL, 3.4 mmol) in dichloromethane (9 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen, Add trifluoroacetic acid (4 mL). After 1 hour, warm to ambient temperature. After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. 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 (85 mg, 57%).

Workup

  1. temperatureCool in an ice bath
  2. customdegas
  3. additionAdd trifluoroacetic acid (4 mL)
  4. waitAfter 3 hours
  5. custompurge with hydrogen sulfide (gas) for about 10 minutes
  6. filtrationFilter
  7. customevaporate in vacuo
  8. customto give a residue
  9. customevaporate in vacuo
  10. customto give a residue
  11. customTriturate the residue with hexane

Sources & evidence

ORD record
ord-5ae5529245274703a3c1f8b6e322927e
Source dataset
uspto-grants-2002_03
Patent number
US06352976B1

Linked notes

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