Trifluoroacetic acid → HCID 86691849, compound

HRID 1616234Notes

Reaction equation

HRID 1616234 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:18]=[C:17]([C:19](O)([CH3:21])[CH3:20])[CH:16]=[CH:15][C:14]=3[CH3:23])=[CH:10][CH:11]=2)[N:6]([CH3:24])[C:5]1=[O:25].[N-:28]=[N+:29]=[N-:30].[Na+].FC(F)(F)C(O)=O>C(Cl)Cl.CCOC(C)=O>[N:28]([C:19]([C:17]1[CH:16]=[CH:15][C:14]([CH3:23])=[C:13]([C:9]2[N:8]=[C:7]3[N:6]([CH3:24])[C:5](=[O:25])[N:4]([CH2:3][C:2]([CH3:1])([CH3:26])[CH3:27])[C:12]3=[CH:11][CH:10]=2)[CH:18]=1)([CH3:20])[CH3:21])=[N+:29]=[N-:30]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 54761054HCID 54761054, compound

Product 1

HCID 86691849HCID 86691849, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 14-2 (1.2 g, 3.3 mmol) and sodium azide (0.42 g, 6.5 mmol) in DCM (8 mL) at −78 C was added a solution of trifluoroacetic acid (1.0 mL, 13 mmol) in DCM (0.25 mL). The reaction mixture was allowed to slowly warm to room temperature over 15 hours. The reaction was diluted in EtOAc and washed with water, brine, dried over sodium sulfate, filtered and concentrated to give product. HRMS (M+H)+: observed=393.2389, calculated=393.2397.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give product

Sources & evidence

ORD record
ord-ebbbeb50be904621a4bba92c89951508
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

Loading…