Trifluoroacetic acid → HCID 68943136, compound

HRID 576293Notes

Reaction equation

HRID 576293 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:8]([C:20]([NH2:22])=O)=[C:7]2[CH2:23][CH2:24][CH2:25][O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.FC(F)(F)C(O)=O>O1CCCC1.ClCCl.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:8]([C:20]#[N:22])=[C:7]2[CH2:23][CH2:24][CH2:25][O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 68943112HCID 68943112, compound

Product 1

HCID 68943136HCID 68943136, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of EXAMPLE 581B (545 mg) in tetrahydrofuran (5 mL) and dichloromethane (1 ml) was added triethylamine (1 ml) followed by trifluoroacetic acid (1 ml) dropwise. After the addition, the mixture was stirred for 3 hours at 0° C. The mixture was diluted with ethyl acetate (200 mL) and water (80 mL). The aqueous layer was extracted with ether. The combined organic extracts were washed with water (×3), brine and dried over Na2SO4. After filtration, concentration of the solvent gave EXAMPLE 581C.

Workup

  1. additionAfter the addition
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organic extracts were washed with water (×3), brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration of the solvent
  6. customgave EXAMPLE 581C

Sources & evidence

ORD record
ord-2764813883854df091b40d22f44cce9e
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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