Toluene → HCID 178423493, compound

HRID 1759700Notes

Reaction equation

HRID 1759700 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:46]=[CH:45][C:12]2[NH:13][C:14]([NH:16][C@H:17]([C:38]([O:40]C(C)(C)C)=[O:39])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29](=[O:37])[NH:30][C:31]4[NH:32][CH2:33][CH2:34][CH2:35][N:36]=4)=[CH:21][CH:20]=3)=[N:15][C:11]=2[CH:10]=1.C1(C)C=CC=CC=1>ClCCl>[CH3:8][C:9]1[CH:46]=[CH:45][C:12]2[NH:13][C:14]([NH:16][C@H:17]([C:38]([OH:40])=[O:39])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][C:29](=[O:37])[NH:30][C:31]4[NH:32][CH2:33][CH2:34][CH2:35][N:36]=4)=[CH:21][CH:20]=3)=[N:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 178423492HCID 178423492, compound

Product 1

HCID 178423493HCID 178423493, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of trifluoroacetic acid is added to 20 mg of the ester 4-5b in 3 ml of dichloromethane, followed by agitating for 5 hours at ambient temperature then adding toluene. After evaporating under reduced pressure, taking up in dichloromethane and crystallizing by adding an Et2O/pentane mixture, 15 mg of 4-6b is obtained.

Workup

  1. customAfter evaporating under reduced pressure
  2. customcrystallizing
  3. additionby adding an Et2O/pentane mixture

Sources & evidence

ORD record
ord-9795a6d54a404995abe2977fc8ec0c33
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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