Toluene → HCID 15985611, compound

HRID 1668426Notes

Reaction equation

HRID 1668426 reaction equation
[CH2:1]([NH:9][C:10]([C@H:12]1[N:16]2[C:17](=[O:31])[C@@H:18]([NH:23][C:24](=[O:30])[C@@H:25]([N:27](C)[CH3:28])[CH3:26])[CH2:19][CH:20]=[CH:21][CH2:22][C@H:15]2[CH2:14][CH2:13]1)=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([NH:9][C:10]([C@H:12]1[N:16]2[C:17](=[O:31])[C@@H:18]([NH:23][C:24](=[O:30])[C@@H:25]([NH:27][CH3:28])[CH3:26])[CH2:19][CH:20]=[CH:21][CH2:22][C@H:15]2[CH2:14][CH2:13]1)=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 66995328HCID 66995328, compound

Product 1

HCID 15985611HCID 15985611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Product 11I is reconstituted in 20% trifluoroacetatic acid in dichloromethane (50 mL). Stirring until reaction complete by HPLC. Toluene is added and concentrated to an amber oil. The product is dissolved in dichloromethane and washed with saturated bicarb followed by drying over anhydrous magnesium sulfate, filtering and concentrating. HPLC purification to yield 12. LCMS characterization ES+413.1 (m+1).

Workup

  1. concentrationconcentrated to an amber oil
  2. dissolutionThe product is dissolved in dichloromethane
  3. washwashed with saturated bicarb
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. concentrationconcentrating
  7. customHPLC purification

Sources & evidence

ORD record
ord-31b451374fec4b13ac2003712bcea3bb
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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