Trifluoroacetic acid → HCID 66662412, compound

HRID 2193477Notes

Reaction equation

HRID 2193477 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]([C:29](=[O:31])[NH2:30])=[C:15]([NH:17][C:18](=[O:28])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[F:27])[S:16][C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][C:18]([NH:17][C:15]2[S:16][C:10]3[CH2:9][NH:8][CH2:13][CH2:12][C:11]=3[C:14]=2[C:29]([NH2:30])=[O:31])=[O:28])=[C:21]([F:27])[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66662868HCID 66662868, compound

Product 1

HCID 66662412HCID 66662412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Starting material 19 (3.2 g, 22% content, 1.5 mmol) was dissolved in 25 ml dried DCM and trifluoro acetic acid (TFA, 8.0 ml, 104 mmol) was added. The reaction was stirred at ambient temperature for 30 Min. The solvent was reduced in vacuo and the crude product was purified at the Flashmaster (Method 1). The isolated product was not sufficiently pure and was therefore purified again at the prep. HPLC (Method 4). The pure fractions were combined and the solvent was reduced. The desired product 20 was thereby isolated as a brown solid (236 mg, 42%).

Workup

  1. customthe crude product was purified at the Flashmaster (Method 1)
  2. customwas therefore purified again at the prep

Sources & evidence

ORD record
ord-9085779cd6324e10a95ba0da3d25f715
Source dataset
uspto-grants-2012_12
Patent number
US08329907B2

Reaction notes

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