Trifluoroacetic acid → HCID 18440724, compound

HRID 457744Notes

Reaction equation

HRID 457744 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:32])[N:13]([CH2:20][CH2:21][CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[NH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:13]1[C:12](=[O:32])[C:11]2[C:15](=[CH:16][CH:17]=[CH:18][C:10]=2[NH:9][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:8])[C:14]1=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18440734HCID 18440734, compound

Product 1

HCID 18440724HCID 18440724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.53 g (7.39 mmol) of tert-Butyl 4-(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butylcarbamate are dissolved in 150 ml of dichloromethane, and a solution of 10 ml of trifluoroacetic acid in 50 ml of dichloromethane is added at 0° C. The reaction mixture is slowly warmed to RT and stirred overnight. The reaction mixture is then concentrated and the oily residue is stored at 5° C. overnight. Dichloromethane and a little ethanol are added to the residue, which is now partially crystalline, and the mixture is filtered. This gives 3.44 g (95% of theory) of the desired product as a solid.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. waitthe oily residue is stored at 5° C. overnight
  3. additionDichloromethane and a little ethanol are added to the residue, which
  4. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-fffa1afa1d0548d8980d293c7c7afc6f
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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