HCID 131730718, compound → Trifluoroacetic acid

HRID 451905Notes

Reaction equation

HRID 451905 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].Cl[C:9]1[C:10]([F:45])=[C:11]([C@@H:15]([C@@H:24]2[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:44])[NH:31][CH:32]([CH2:36][C@H:37]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39][CH2:38]3)[CH2:33][NH:34][CH3:35])[CH2:25]2)[O:16][CH2:17][CH2:18][NH:19][C:20](=[O:23])[O:21][CH3:22])[CH:12]=[CH:13][CH:14]=1>CO.[Pd]>[F:45][C:10]1[CH:9]=[CH:14][CH:13]=[CH:12][C:11]=1[C@@H:15]([C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30](=[O:44])[NH:31][CH:32]([CH2:36][C@H:37]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39][CH2:38]2)[CH2:33][NH:34][CH3:35])[CH2:25]1)[O:16][CH2:17][CH2:18][NH:19][C:20](=[O:23])[O:21][CH3:22].[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

5

Reactant 1

HCID 131730718HCID 131730718, compound

Product 2

HCID 6422Trifluoroacetic acidYield 89.7%HCID 68713114HCID 68713114, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-((1R)-(3-chloro-2-fluorophenyl)((3R)-1-(1-(methylamino)-3-((R)-oxepan-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate TFA salt (12 mg, 0.018 mmol) in MeOH (5 mL) was added HCO2NH4 (1.2 g) and 10% Pd/C (50 mg). The mixture was stirred for 1 h at rt. The catalyst was filtered off and concentrated, the residue was purified on preparative HPLC to give methyl 2-((1R)-(2-fluorophenyl)((3R)-1-(1-(methylamino)-3-((R)-oxepan-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate as a TFA salt (1.84 mg, 16%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationconcentrated
  3. customthe residue was purified on preparative HPLC

Sources & evidence

ORD record
ord-74afff53931743649267f1e9e9ff2991
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…