Trifluoroacetic acid → HCID 66810301, compound

HRID 1477325Notes

Reaction equation

HRID 1477325 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH:15]C(=O)OC(C)(C)C)[CH2:13][C@@H:12]([N:23]2[CH2:30][C:29]3[CH2:28][NH:27][N:26]([S:31]([CH:34]4[CH2:36][CH2:35]4)(=[O:33])=[O:32])[C:25]=3[CH2:24]2)[CH2:11][O:10]1.[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH2:15])[CH2:13][C@@H:12]([N:23]2[CH2:30][C:29]3[CH2:28][NH:27][N:26]([S:31]([CH:34]4[CH2:36][CH2:35]4)(=[O:32])=[O:33])[C:25]=3[CH2:24]2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666436HCID 86666436, compound

Product 1

HCID 66810301HCID 66810301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the intermediate obtained in Step A above (52 mg, 0.099 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (1 mL) at room temperature. After 1.5 h, the reaction mixture was concentrated and purified on reverse phase HPLC using H2O/acetonitrile containing 0.05 TFAv/v, to give the title compound. 1H NMR (500 MHz, CD3OD): δ 1.21-1.27 (m, 2H); 1.38-1.43 (m, 2H); 2.06 (q, 1H, J=14 Hz); 2.73-2.79 (m, 1H); 2.29-3.06 (m, 1H); 3.57-3.64 (m, 1H); 3.74 (t, 1H, J=12 Hz); 3.81-3.90 (m, 1H); 4.44-4.54 (m, 3H); 4.69 (d, 1H, J=12 Hz); 4.71-4.81 (m, 2H); 7.18-7.26 (m, 2H); 7.27-7.32 (m, 1H); 7.74 (s, 1H). LC-MS: 425.21 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified on reverse phase

Sources & evidence

ORD record
ord-215b2ed3ca214551b20d2c597a535473
Source dataset
uspto-grants-2016_08
Patent number
US09403790B2

Reaction notes

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