Trifluoroacetic acid → HCID 90412663, compound

HRID 1522003Notes

Reaction equation

HRID 1522003 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][CH2:19][N:20]([C:23]([C@H:25]5[CH2:29][C@@H:28]([OH:30])[CH2:27][N:26]5C(OC(C)(C)C)=O)=[O:24])[CH2:21][CH:22]=4)=[CH:16][C:9]=23)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:38][CH3:39])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][CH2:19][N:20]([C:23]([C@H:25]5[CH2:29][C@@H:28]([OH:30])[CH2:27][NH:26]5)=[O:24])[CH2:21][CH:22]=4)=[CH:16][C:9]=23)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90412659HCID 90412659, compound

Product 1

HCID 90412663HCID 90412663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 240A (100 mg, 0.186 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.2 mL, 2.60 mmol) and the mixture was stirred at room temperature for 4 hours and concentrated. The residue was dissolved in dichloromethane (2 mL) and treated with 2M hydrogen chloride in ether (2.5 mL) and filtered. The solid was washed with diethyl ether and concentrated to obtain the title compound as the hydrochloride salt. 1H NMR (500 MHz, DMSO-d6) δ 1.70-1.80 (m, 1H), 2.53-2.79 (m, 2H), 3.09-3.32 (m, 2H), 4.60-4.06 (m, 7H) 4.37-4.43 (m, 2H), 4.44 (dd, J=38.4, 9.5 Hz, 1H), 4.57-4.77 (m, 1H), 6.44 (bs, 1H), 6.62-6.69 (m, 1H), 7.01-7.38 (m, 3H), 8.29 (d, J=5.3 Hz, 1H), 8.46-8.80 (m, 1H), 10.24 (bs, 1H), 12.57-12.65 (m, 1H). MS (ESI(+)) m/e 437 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (2 mL)
  3. additiontreated with 2M hydrogen chloride in ether (2.5 mL)
  4. filtrationfiltered
  5. washThe solid was washed with diethyl ether
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a74675e644694604a1f98afbe17be10f
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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