Trifluoroacetic acid → HCID 66810543, compound

HRID 1619910Notes

Reaction equation

HRID 1619910 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[C:25](=[N:26][N:27]([S:31]([CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)(=[O:33])=[O:32])[CH:28]=3)[CH2:24]2)[CH2:11][O:10]1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>ClCCl>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[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[C:25](=[N:26][N:27]([S:31]([CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)(=[O:32])=[O:33])[CH:28]=3)[CH2:24]2)[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86641698HCID 86641698, compound

Product 1

HCID 66810543HCID 66810543, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the intermediate obtained in Step A above (90 mg, 0.16 mmol) in dichloromethane (6 mL) was treated with trifluoroacetic acid (3 mL) at room temperature. After 1.5 h, the reaction mixture was concentrated to give the title compound. 1H NMR (500 MHz, CD3OD): δ 1.61-1.74 (m, 4H); 1.92-2.08 (m, 4H); 2.11 (q, 1H, J=12 Hz); 2.78-2.84 (m, 1H); 3.68 (td, 1H, J=12, 4 Hz); 3.78 (t, 1H, J=12 Hz); 3.88-3.96 (m, 1H); 4.02-4.10 (m, 1H); 4.49-4.67 (m, 5H); 4.71 (d, 1H, J=12 Hz); 7.19-7.27 (m, 2H); 7.28-7.33 (m, 1H); 8.09 (s, 1H). LC-MS: 453.04 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-83ccdfc0fa204dc781abc4da23edeb53
Source dataset
uspto-grants-2014_07
Patent number
US08772328B2

Reaction notes

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