4-Nitrophenol → HCID 11573689, compound

HRID 1162503Notes

Reaction equation

HRID 1162503 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([NH:10][S:11]([N:14]2[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:15]2[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:17]1[CH2:18][N:14]2[C@H:15]([C:20](=[O:21])[N:10]([C:4]3[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=3[CH3:23])[S:11]2(=[O:13])=[O:12])[CH2:16]1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 59520084HCID 59520084, compound

Product 1

HCID 11573689HCID 11573689, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4B (57 mg, 0.158 mmol) in 5 mL of acetonitrile at rt was added DCC (33 mg, 0.158 mmol) followed by p-nitrophenol (44 mg, 0.317 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 concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc/Hexanes, 50:50 and 75:25) to afford the title compound (28 mg) as a beige solid. 1H NMR (DMSO-d6) δ 2.25, 2.28 (s, 3H), 2.31-2.38 (m, 2H), 3.46-3.50 (m, 1H), 3.86 (d, J=12.1, 1H), 4.24 (s, 1H), 4.93, 5.07 (d, J=7.2, 1H), 5.42, 5.51 (s, 1H), 7.27, 7.50 (d, J=8.2, 1H), 7.98, 8.03 (d, J=8.3, 1H); 13C NMR (DMSO-d6) δ 15.06, 15.74, 37.57, 60.55, 60.72, 64.84, 65.37, 68.30, 114.37, 115.61, 128.85, 129.59, 132.65, 132.79, 134.96, 136.96, 138.35, 139.36, 169.16; 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, 2.62 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 254 nm, 2.45 min retention time (100%); HPLC c) column: Daicel Chiralcel OD 4.6×250 mm, Isocratic 25% Isopropanol/Hexanes, 30 min, 1 mL/min, UV detection at 220 nm, 12.65 min retention time (99%); MS (ES) m/z 340 [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. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, EtOAc/Hexanes, 50:50 and 75:25)

Sources & evidence

ORD record
ord-31ff9cbaf9434dc28a04a7a48cf6f7d1
Source dataset
uspto-grants-2010_10
Patent number
US07820702B2

Reaction notes

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