Trifluoroacetic acid → HCID 86713385, compound

HRID 921266Notes

Reaction equation

HRID 921266 reaction equation
[F:1][C:2]([F:44])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][C@@H:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[N:23]1)[C@H:6]([CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:44][C:2]([F:1])([F:43])[CH2:3][CH2:4][C@@H:5]([C:20](=[O:42])[NH:21][C@@H:22]1[C:28](=[O:29])[NH:27][C:26]2[C:30]([CH3:34])=[CH:31][CH:32]=[CH:33][C:25]=2[C:24]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=2)=[N:23]1)[C@H:6]([CH2:14][CH2:15][C:16]([F:17])([F:18])[F:19])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86713386HCID 86713386, compound

Product 1

HCID 86713385HCID 86713385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask, a solution of Intermediate 1A (3.7 g, 5.86 mmol) in DCM (25 mL) was treated with TFA (25 mL) and the resulting pale orange solution was stirred at room temperature for 1.5 hours. The reaction mixture was then concentrated to give Intermediate 1B. HPLC: RT=3.12 min (H2O/MeOH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=4 min, wavelength=220 nm). MS(ES): m/z=576.3 (M+H)+. 1H NMR (400 MHz, methanol-d4) δ 7.54 (t, J=4.5 Hz, 1H), 7.49-7.29 (m, 3H), 7.28-7.15 (m, 3H), 5.38 (br. s., 1H), 2.89 (td, J=10.3, 3.7 Hz, 1H), 2.67 (td, J=9.9, 4.2 Hz, 1H), 2.56-2.38 (m, 1H), 2.48 (s, 3H), 2.34-2.13 (m, 3H), 2.00-1.71 (m, 4H).

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-5e0ac92e96ef4c6eb2d3fdc16033d0ee
Source dataset
uspto-grants-2016_03
Patent number
US09273014B2

Reaction notes

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