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 1264552Notes

Reaction equation

HRID 1264552 reaction equation
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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

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-866b9302256e46dbad140583cd1b7690
Source dataset
uspto-grants-2003_04
Patent number
US06544980B2

Reaction notes

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