Carbon Tetrachloride → 2-(4-(2-Mercapto-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid

HRID 1264552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264552
C([O:5][C:6](=[O:53])[CH:7]([N:12]1[C:18](=[O:19])[CH:17]([NH:20][C:21](=[O:48])[CH:22]([S:38]CC2C=CC(OC)=CC=2)[CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])[CH2:16][C:15]2[CH:49]=[CH:50][CH:51]=[CH:52][C:14]=2[CH2:13]1)[CH2:8][CH:9]([CH3:11])[CH3:10])(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:38][CH:22]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:28](=[O:37])[C:29]2=[CH:36][CH:35]=[CH:34][CH:33]=[C:30]2[C:31]1=[O:32])[C:21]([NH:20][CH:17]1[C:18](=[O:19])[N:12]([CH:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]([OH:53])=[O:5])[CH2:13][C:14]2[CH:52]=[CH:51][CH:50]=[CH:49][C:15]=2[CH2:16]1)=[O:48]

Komponenten

6

Edukt 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 538676092-(4-(2-(p-Methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester

Produkt 1

HCID 186125202-(4-(2-Mercapto-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15337Mercuric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine 2-(4-(2-(p-methoxybenzylthio)-6-phthalimidohexanoyl-amino)-3-oxo-1,3,4,5-tetrahydro-benzo[c]azepin-2-yl)-4-methyl-valeric acid t-butyl ester (0.20 mmol), mercury (II) acetate (0.084 g, 0.26 mmol), and anisole (0.23 mL, 2.1 mmol) in dichloromethane (6.6 mL). Cool in an ice bath and degas by repeatedly cycles of vacuum and filling the vessel with nitrogen gas. Add trifluoroacetic acid (2.5 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 the title compound.

Aufarbeitung

  1. temperatureCool in an ice bath
  2. customdegas by repeatedly cycles of vacuum
  3. waitAfter 3 hours
  4. custompurge with hydrogen sulfide (gas) for about 10 minutes
  5. filtrationFilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-866b9302256e46dbad140583cd1b7690
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544980B2

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