4-Nitrophenol → HCID 11646102, compound

HRID 1162501Notes

Reaction equation

HRID 1162501 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([NH:10][S:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([OH:19])[C@@:15]2([CH3:23])[C:20](O)=[O:21])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1CCC(N=C=NC2CCCCC2)CC1.C1C([N+]([O-])=O)=CC=C(O)C=1>C(#N)C>[OH:19][C@@H:16]1[CH2:17][CH2:18][N:14]2[C@:15]1([CH3:23])[C:20](=[O:21])[N:10]([C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=1[CH3:24])[S:11]2(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 59520077HCID 59520077, compound

Product 1

HCID 11646102HCID 11646102, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3D (70 mg, 0.187 mmol) in 4 mL of acetonitrile at rt was added DCC (39 mg, 0.187 mmol) followed by p-nitrophenol (53 mg, 0.374 mmol). The suspension was refluxed for 1 h, cooled to rt and filtered. The filtrate was concentrated under reduced pressure and the residue dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc/Hexanes, 50:50) to afford the title compound (48 mg) as a yellow foam. 1H NMR (CD3OD) δ 1.59, 1.64 (s, 3H), 2.14-2.18 (m, 1H), 2.33-2.39 (m, 4H), 3.62-3.68 (m, 1H), 3.98-4.07 (m, 1H), 4.29, 4.31 (d, J=3.3, 1H), 7.45, 7.52 (d, J=8.3, 1H), 7.81, 7.82 (d, J=8.3, 1H); 13C NMR (CD3OD) δ 16.11, 16.25, 22.94, 23.24, 34.60, 50.21, 50.67, 77.10, 77.26, 82.46, 82.66, 116.44, 116.55, 129.95, 131.05, 133.22, 133.35, 136.32, 138.82, 140.34, 141.02, 169.27; HPLC a) column: Phenominex LUNA C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA; 1 min hold, 4 mL/min UV detection at 220 nm, 2.90 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold; 4 mL/min, UV detection at 220 nm, 2.75 min. retention time (98%); HPLC c) column: Daicel Chiralcel OD 4.6×250 mm, Isocratic 25% Isopropanol/Hexanes, 30 min, 1 mL/min, UV detection at 220 nm, 6.96 min retention time (98%); MS (ES) m/z 356 [M+H]+.

Workup

  1. temperatureThe suspension was refluxed for 1 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, EtOAc/Hexanes, 50:50)

Sources & evidence

ORD record
ord-ba4b2ae428ea437f90a0cad94d4b6138
Source dataset
uspto-grants-2010_10
Patent number
US07820702B2

Reaction notes

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