Trifluoroacetic acid → HCID 54137645, compound

HRID 1701675Notes

Reaction equation

HRID 1701675 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:42])[CH2:34][S:35][C:36]2[N:40]([CH3:41])[N:39]=[N:38][N:37]=2)[C:17]([O:19]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:18])[C:13]1=[O:43])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCCCCC>C1(OC)C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:42])[CH2:34][S:35][C:36]2[N:40]([CH3:41])[N:39]=[N:38][N:37]=2)[C:17]([OH:19])=[O:18])[C:13]1=[O:43])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 86736894HCID 86736894, compound

Product 1

HCID 54137645HCID 54137645, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

The product from Example 13 above was dissolved in 1 ml of anisole. At 0° 1 ml of trifluoracetic acid was added. After 15 minutes at 0°, hexane was added. The solvents were removed under reduced pressure. Ether was added to the residue. The resulting slurry was filtered to provide 210 mg (53% from bromo derivative) of the title product: nmr (CDCl3) δ 2.10 and 2.27 (s, 3, CH3), 3.92 (s, 3, N--CH3), 4.3 (m, 2, --CH2S), 3.50 (m, 2, C4 --H), 5.00 (m, 1, C3 --H), 4.50 (s, 2, side chain CH2) and 7.2 (b, ArH).

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionEther was added to the residue
  3. filtrationThe resulting slurry was filtered

Sources & evidence

ORD record
ord-1cea9023ffe5447fa07e0c3acf58ce4b
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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