Carbon Tetrachloride → HCID 23502986, compound

HRID 1835665Notes

Reaction equation

HRID 1835665 reaction equation
[C:1]1([CH2:7][CH:8]([N:16]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH:18]([NH:29][C:30](=[O:57])[CH:31]([S:47]CC3C=CC(OC)=CC=3)[CH2:32][CH2:33][CH2:34][CH2:35][N:36]3[C:44](=[O:45])[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:37]3=[O:46])[C:17]2=[O:58])[C:9]([O:11]C(C)(C)C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>ClCCl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[C:1]1([CH2:7][CH:8]([N:16]2[CH2:22][CH2:21][CH:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH:18]([NH:29][C:30](=[O:57])[CH:31]([SH:47])[CH2:32][CH2:33][CH2:34][CH2:35][N:36]3[C:37](=[O:46])[C:38]4[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:44]3=[O:45])[C:17]2=[O:58])[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 23502988HCID 23502988, compound

Product 1

HCID 23502986HCID 23502986, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine N-[hexahydro-1-[1-(phenylmethyl)-1-t-butoxycarbonylmethyl]-2-oxo-5-phenyl-1H-azepin-3-yl]-1,3-dihydro-a-(p-methoxybenzylthio)-1,3-dioxo-2H-isoindole-2-hexanamide (0.16 g, 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.

Workup

  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

Sources & evidence

ORD record
ord-c2858e4a7a76484a937e9567a13d31a2
Source dataset
uspto-grants-2004_08
Patent number
US06770640B1

Reaction notes

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