Trifluoroacetic acid → HCID 22615022, compound

HRID 843144Notes

Reaction equation

HRID 843144 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23]O.[CH2:25]([SH:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:23][S:33][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 781262-PhenylethanethiolHCID 22615037HCID 22615037, compound

Product 1

HCID 22615022HCID 22615022, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound in Example 11 (20 mg, 0.06 mmol) and phenethyl mercaptan (30 mg) in anhydrous CH2Cl2 (0.9 ml) was added trifluoroacetic acid (TFA, 0.2 ml). The mixture was stirred at room temperature for 2.5 hours. The solvent was removed under reduced pressure. The residue was purified over preparative TLC (CH2Cl2/MeOH=100/1) to give the desired compound (26 mg, 95%) as a colorless oil. FAB-MS: m/z 446 (MH+); 1H-NMR (CDCl3): δ 2.10 (2H, m), 2.32 (3H, s), 2.79-2.97 (6H, m), 3.54 (2H, s), 3.85 (2H, s), 3.90 (2H, s), 6.63 (1H, d, J=7.6 Hz), 7.09-7.30 (3H, m), 7.71 (1H, d, J=7.8 Hz), 8.55 (1H, d, J=2.0 Hz), 8.62 (1H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified over preparative TLC (CH2Cl2/MeOH=100/1)

Sources & evidence

ORD record
ord-8fc0a6c5a7354f7c9b51c9bad2b5b1ec
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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