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

HRID 276114

反応式

HRID 276114 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 155487402-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine収率 58.2%

試薬・触媒・溶媒 2

HCID 15337Mercuric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5ae5529245274703a3c1f8b6e322927e
出典データセット
uspto-grants-2002_03
特許番号
US06352976B1

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