Trifluoroacetic acid → HCID 118269724, compound

HRID 1483217Notes

Reaction equation

HRID 1483217 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:12](=[O:13])[C:11](=[O:14])[C:10]=2[NH:15][C:16]2[S:26][C:19]3[CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH2:23][C:18]=3[C:17]=2[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:12](=[O:13])[C:11](=[O:14])[C:10]=2[NH:15][C:16]2[S:26][C:19]3[CH2:20][N:21]([CH2:24][CH3:25])[CH2:22][CH2:23][C:18]=3[C:17]=2[C:27]([OH:29])=[O:28])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736723HCID 131736723, compound

Product 1

HCID 118269724HCID 118269724, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of compound O3 (293 mg, 0.600 mmol) in methylene chloride (12 mL) and toluene (3 mL) at room temperature under nitrogen was added trifluoroacetic acid (6.91 g, 60.6 mmol) dropwise over 2 min. After addition, the reaction mixture was stirred for another 2 h. The reaction mixture was diluted with toluene (20 mL) and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with ammonium hydroxide/methanol/methylene chloride (1:14:85) to afford compound O4 as yellow solid (120 mg, 46%): MS (M−H) 430.

Workup

  1. additionAfter addition
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by flash column chromatography on silica gel eluting with ammonium hydroxide/methanol/methylene chloride (1:14:85)

Sources & evidence

ORD record
ord-96df5ff50da9477ea6d971c0e4ba881b
Source dataset
uspto-grants-2016_08
Patent number
US09416141B2

Reaction notes

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