Trifluoroacetic acid → HCID 66810301, compound

HRID 1845825Notes

Reaction equation

HRID 1845825 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][C@@H:12]([N:14]2[CH2:21][C:20]3[CH2:19][NH:18][N:17]([S:22]([CH:25]4[CH2:27][CH2:26]4)(=[O:24])=[O:23])[C:16]=3[CH2:15]2)[CH2:11][O:10][C@@H:9]1[C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[F:35])(C)(C)C.[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:35][C:29]1[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:28]=1[C@@H:9]1[C@@H:8]([NH2:7])[CH2:13][C@@H:12]([N:14]2[CH2:21][C:20]3[CH2:19][NH:18][N:17]([S:22]([CH:25]4[CH2:27][CH2:26]4)(=[O:23])=[O:24])[C:16]=3[CH2:15]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-9b68b4153e9a46848d23cfee0374d6b5
Source dataset
uspto-grants-2015_02
Patent number
US08951965B2

Reaction notes

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