(S)-4-(((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)-2-nitrophenyl Acetate → (S)-2-Amino-4-(((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)phenyl Acetate

HRID 2370858Notes

Reaction equation

HRID 2370858 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:31])[NH:12][C@H:13]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[CH:7][C:6]=1[N+:32]([O-])=O)(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:31])[NH:12][C@H:13]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=2)=[CH:7][C:6]=1[NH2:32])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86687996(S)-4-(((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)-2-nitrophenyl Acetate

Product 1

HCID 86687997(S)-2-Amino-4-(((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)phenyl Acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask purged with N2 was added 10% Pd/C (20.29 mg, 0.019 mmol) and under a N2 atmosphere (S)-4-(((3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamoyl)-2-nitrophenyl acetate (91 mg, 0.191 mmol) in EtOAc (10 mL) was added. The solution was purged for a further 2 min, then capped with a balloon of H2. After 5 h, the reaction was filtered through a pad of Celite® brand filter agent and the Celite® brand filter agent rinsed with EtOAc. The filtrate was concentrated in vacuo and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (4 g), eluting with 0 to 75% EtOAc in hexane, to provide the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 9.85 (s, 1H), 8.35-8.54 (m, 2H), 8.19 (s, 1H), 7.66 (d, J=2.2 Hz, 1H), 7.59 (dd, J=8.5, 2.0 Hz, 1H), 7.55 (s, 4H), 7.38-7.47 (m, 1H), 7.32 (dt, J=8.4, 4.3 Hz, 1H), 7.04 (d, J=8.3 Hz, 1H), 6.62 (dd, J=6.9, 2.0 Hz, 1H), 2.20 (s, 3H). MS (ESI pos. ion) m/z: 448.1 (M+H).

Workup

  1. customTo a round bottom flask purged with N2
  2. customThe solution was purged for a further 2 min
  3. customcapped with a balloon of H2
  4. filtrationthe reaction was filtered through a pad of Celite® brand
  5. filtrationfilter agent
  6. filtrationthe Celite® brand filter agent
  7. washrinsed with EtOAc
  8. concentrationThe filtrate was concentrated in vacuo
  9. customchromatographed through a Redi-Sep® pre-packed silica gel column (4 g)
  10. washeluting with 0 to 75% EtOAc in hexane

Sources & evidence

ORD record
ord-a8489d5286a548eaa26c2905e6308c60
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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