Trifluoroacetic acid → HCID 178484146, compound

HRID 1159359Notes

Reaction equation

HRID 1159359 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]([CH2:17][C@H:18]1[CH2:21][C@H:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:25][CH:24]=2)[CH2:19]1)C(=O)OC(C)(C)C>ClCCl>[CH3:8][NH:9][CH2:17][C@H:18]1[CH2:21][C@H:20]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:25][CH:24]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178484147HCID 178484147, compound

Product 1

HCID 178484146HCID 178484146, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8.6 mL, 111 mmol) was added to a solution of compound 9 (5.56 g, 15 mmol) in dichloromethane (50 mL). The reaction mass was stirred at room temperature for 24 h and evaporated in vacuo. The residue was diluted with water (50 mL), and the obtained solution was extracted with CH2Cl2. The organic layer was discarded. The aqueous one was alkalized with 10 N NaOH to pH 12 and extracted with CHCl3 (3×100 mL). The combined extracts were dried and evaporated to afford the title compound (3 g, 74%) as a yellow oil. LCMS-data: M+H 275.2, 276.2 (calc. 274.4). 1H NMR-data (DMSO-d6): 7.16 (d, 2H, Ph, J=8.6); 6.72 (d, 2H, Ph, J=8.6); 4.65-4.78 (m, 1H); 3.46 (s, 2H, CH2); 2.56 (d, 2H, CH2, J=7.6); 2.34-2.41 (m, 4H); 2.28 (s, 3H, NCH3); 2.00-2.30 (m, 5H); 1.60-1.71 (m, 4H).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with water (50 mL)
  3. extractionthe obtained solution was extracted with CH2Cl2
  4. extractionextracted with CHCl3 (3×100 mL)
  5. customThe combined extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-7e746e0e89fc4c59bf6091775880ef9b
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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