Trifluoroacetic acid → HCID 135885185, compound

HRID 2110601Notes

Reaction equation

HRID 2110601 reaction equation
C([NH:5][C:6]([NH:8][C:9]1([CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:5][C:6]([NH:8][C:9]1([CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[C:11]([C:20]2[NH:25][C:24]3[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][C:23]=3[S:22](=[O:36])(=[O:35])[N:21]=2)[C:10]1=[O:37])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136383510HCID 136383510, compound

Product 1

HCID 135885185HCID 135885185, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 57 (8 mg, 0.013 mmol) in dichloromethane (0.3 mL) was added trifluoroacetic acid (0.3 mL). The solution was stirred at room temperature for 18 h and then concentrated in vacuo. Column chromatography on silica (5% methanol/dichloromethane) afforded the title compound as an off-white solid (7 mg, 100%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.67 (dd, J=6.43, 3.86 Hz, 6H), 0.83-1.07 (m, 2H), 1.17-1.31 (m, 1H), 1.46-1.62 (m, 1H), 1.66-1.83 (m, 1H), 2.99 (s, 3H), 5.40 (s, 2H), 6.51 (s, 1H), 7.23-7.33 (m, 2H), 7.34-7.43 (m, 3H), 7.46 (d, J=2.21 Hz, 1H), 7.97 (d, J=8.09 Hz, 1H), 9.86 (s, 1H), 15.47 (s, 1H); MS m/z 562.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2622f1e14d16498e8d7dd17801dcafef
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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