Trifluoroacetic acid → HCID 567473, compound

HRID 1958282Notes

Reaction equation

HRID 1958282 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]([OH:30])[CH2:16][N:17]2[C:29]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:19]1[C:18]2[N:17]([CH2:16][CH:15]([OH:30])[CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9866219HCID 9866219, compound

Product 1

HCID 567473HCID 567473, compoundYield 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At rt to a solution of Example 2 (3.4 g, 8.30 mmol) in DCM (120 mL) is added TFA (30 mL). The resulting mixture is stirred at rt for 30 min. Concentration in vacuo gives an oily residue. Flash chromatography on a 7×18 cm2 column of SiO2 using DCM:MeOH:TEA (40:5:3) as eluting solvent and removal of the solvent gives the title compound (3.12 g, 92%) as a white foam. Slow addition of HCl (30 mL, 4 eq, 1M in Et2O) into a solution of the above compound in EtOH (40 mL) gives the hydrochloride salt of the title compound as beige crystals in a quantitative yield.

Workup

  1. concentrationConcentration in vacuo
  2. customgives an oily residue
  3. washas eluting
  4. customsolvent and removal of the solvent

Sources & evidence

ORD record
ord-1f0be140817f460c9545ce4a991231f4
Source dataset
uspto-grants-2013_04
Patent number
US08410110B2

Reaction notes

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