Trifluoroacetic acid → HCID 9803821, compound

HRID 353198Notes

Reaction equation

HRID 353198 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[CH2:11][N:12]([CH2:19][C:20]1[CH:36]=[CH:35][C:23]([O:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28]C(C)(C)C)=[O:27])=[CH:22][CH:21]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[CH2:11][N:12]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][C:25]([CH3:34])([CH3:33])[C:26]([OH:28])=[O:27])=[CH:35][CH:36]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22708223HCID 22708223, compound

Product 1

HCID 9803821HCID 9803821, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.09 g (14.00 mmol) of the compound from Example 3-1 and 35 ml of trifluoroacetic acid are stirred at room temperature in 35 ml of dichloromethane for 2 hours. The solvent is distilled off and the residue is then dissolved in ethyl acetate, washed with water, 20 percent strength sodium acetate solution and saturated sodium chloride solution and then dried over magnesium sulphate. The solvent is removed and the residue is then purified by flash chromatography on silica gel (dichloromethane→dichloromethane/ethyl acetate 5:1→2:1→1:1): The gives the target compound in a yield of 82%.

Workup

  1. distillationThe solvent is distilled off
  2. dissolutionthe residue is then dissolved in ethyl acetate
  3. washwashed with water, 20 percent strength sodium acetate solution and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is removed
  6. customthe residue is then purified by flash chromatography on silica gel (dichloromethane→dichloromethane/ethyl acetate 5:1→2:1→1:1)
  7. customThe gives the target compound in a yield of 82%

Sources & evidence

ORD record
ord-3736b013968d4cec8b3be8bd3243a30c
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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