Trifluoroacetic acid → HCID 86641702, compound

HRID 1477327Notes

Reaction equation

HRID 1477327 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[C@@H:15]([NH:16]C(=O)OC(C)(C)C)[CH2:14][C@@H:13]([N:24]2[CH2:31][C:30]3[C:26](=[N:27][N:28]([S:32]([CH:35]4[CH2:37][CH2:36]4)(=[O:34])=[O:33])[CH:29]=3)[CH2:25]2)[CH2:12][O:11]1.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>ClCCl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[C@@H:15]([NH2:16])[CH2:14][C@@H:13]([N:24]2[CH2:31][C:30]3[C:26](=[N:27][N:28]([S:32]([CH:35]4[CH2:37][CH2:36]4)(=[O:34])=[O:33])[CH:29]=3)[CH2:25]2)[CH2:12][O:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86641703HCID 86641703, compound

Product 1

HCID 86641702HCID 86641702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product obtained in Step A above (74 mg, 0.14 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 01.18-1.24 (m, 2H); 1.35-1.40 (m, 2H); 2.12 (q, 1H, J=12 Hz); 2.79-2.86 (m, 1H); 2.92-2.98 (m, 1H); 3.64 (td, 1H, J=12, 6 Hz); 3.79 (t, 1H, J=12 Hz); 3.90-3.98 (m, 1H); 4.48-4.54 (m, 1H); 4.57-4.72 (m, 5H); 7.25-7.32 (m, 1H); 7.46-7.53 (m, 1H); 8.08 (s, 1H). LC-MS: 443.04 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-cbd939329a664de9977e29be0f39b65d
Source dataset
uspto-grants-2016_08
Patent number
US09403790B2

Reaction notes

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