Toluene → HCID 90120270, compound

HRID 2202553Notes

Reaction equation

HRID 2202553 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:40][CH3:41])[CH:36]=3)[CH:31]=2)=[CH:28][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:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].C1(C)C=CC=CC=1.CCOCC>C(Cl)Cl>[F:45][C:44]([F:47])([F:46])[C:42]([O-:48])=[O:43].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25]1[NH:26][C:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[C:35]([O:40][CH3:41])[CH:36]=3)[CH:31]=2)=[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 90120215HCID 90120215, compound

Product 1

HCID 90120270HCID 90120270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of E1 in DCM (0.2 M) cooled to 0° C. TFA (70 eq.) was slowly added. The reaction mixture was stirred at room temperature for 2 h. Then, solvent was evaporated under reduced pressure to afford an oily residue that was co-evaporated first with toluene then with Et2O to give the title compound as a pale red solid which was used as such in the next step. MS (ES+) C29H31N3O5: 502 (M+H)+.

Workup

  1. customThen, solvent was evaporated under reduced pressure
  2. customto afford an oily residue that

Sources & evidence

ORD record
ord-5f3e2c4fefc64e218da80d3a167d9e7f
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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