Trifluoroacetic acid → HCID 86641702, compound

HRID 1619914Notes

Reaction equation

HRID 1619914 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 1.18-1.24 (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-069d128600ac4f94a3576cbaa96f3c5b
Source dataset
uspto-grants-2014_07
Patent number
US08772328B2

Reaction notes

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