Trifluoroacetic acid → HCID 137178926, compound

HRID 394495Notes

Reaction equation

HRID 394495 reaction equation
FC(F)(F)C(O)=O.[NH2:8][N:9]=[CH:10][NH:11][C:12](=[O:43])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][C@@H:24]([C:36]([O:38]C(C)(C)C)=[O:37])[NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:17][CH:16]=1>C(Cl)Cl>[NH2:8][N:9]=[CH:10][NH:11][C:12](=[O:43])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][C@@H:24]([C:36]([OH:38])=[O:37])[NH:25][C:26]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 137178927HCID 137178927, compound

Product 1

HCID 137178926HCID 137178926, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 ml of trifluoroacetic acid (TFA) (3 times 1 ml over 6 hours) at +5° C. is added to a solution of 70 mg of the ester obtained in Stage A in 2 ml of CH2Cl2, the reaction medium is agitated for 7 hours then evaporated under reduced pressure after the addition of toluene. 0.5 ml of methanol and 1 ml of ethyl acetate are then added, and after filtration, the filtrate is poured into 10 ml of isopropyl ether to which 2 ml of pentane is added. After filtration, the solid is dried under reduced pressure and 30 mg of expected product is obtained.

Workup

  1. customthen evaporated under reduced pressure
  2. additionafter the addition of toluene
  3. addition0.5 ml of methanol and 1 ml of ethyl acetate are then added
  4. filtrationafter filtration
  5. additionthe filtrate is poured into 10 ml of isopropyl ether to which 2 ml of pentane
  6. additionis added
  7. filtrationAfter filtration
  8. customthe solid is dried under reduced pressure

Sources & evidence

ORD record
ord-b4809941e8da438d8c08d91a6adb39dc
Source dataset
uspto-grants-2003_08
Patent number
US06602878B1

Reaction notes

Loading…