Toluene → HCID 90120308, compound

HRID 2202548Notes

Reaction equation

HRID 2202548 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27]([I:31])=[C:28](I)[N:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33].C1(C)C=CC=CC=1.CCOCC>C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:32]([O-:38])=[O:33].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27]([I:31])=[CH:28][NH+:29]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 90120330HCID 90120330, compound

Product 1

HCID 90120308HCID 90120308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of D4 in DCM (0.19 M) cooled to 0° C. was slowly added TFA (35 eq.). The reaction mixture was stirred at 0° C. for 30 min then allowed to warm up to room temperature and stirred for another 2 h. Solvent was evaporated under reduced pressure affording an oily residue was co-evaporated first with toluene then with Et2O to give the title compound as a pale brown solid which was used as such in the next step. MS (ES+) C18H22IN3O4: 472 (M+H)+.

Workup

  1. temperatureto warm up to room temperature
  2. stirringstirred for another 2 h
  3. customSolvent was evaporated under reduced pressure
  4. customaffording an oily residue

Sources & evidence

ORD record
ord-9ea60770dc8d485d84d57edb54bf6871
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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