Ammonium Chloride → HCID 118098726, compound

HRID 708851Notes

Reaction equation

HRID 708851 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=1[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[NH2:20][C:18]1[CH:17]=[CH:16][C:15]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:14]([CH2:13][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH3:12])[CH:19]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 118098706HCID 118098706, compound

Product 1

HCID 118098726HCID 118098726, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15B (2.062 g, 5.34 mmol) in methanol (30 mL) and THF (5 mL) was added zinc (dust) (3.49 g, 53.4 mmol) and ammonium chloride (5.71 g, 107 mmol). The resulting solution was stirred at rt for 18 h. MeOH was removed under reduced pressure, to the residue Na2CO3 (aq, 100 mL) and EtOAc (250 mL) were added, and the suspension was stirred vigorously for 10 min, filtered though glass frit, solid residue was washed with EtOAc (3×150 mL). Combined EtOAc fractions were washed with std. Na2CO3 (aq, 2×100 mL), water (2×100 mL), brine (1×100 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-100% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15C (1.546 g, 4.34 mmol, 81% yield) as an amber oil. MS (ESI) m/z: 357.2 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.28-7.47 (5H, m), 7.00 (1H, d, J=7.28 Hz), 6.56 (1H, d, J=8.03 Hz), 6.38-6.52 (1H, m), 5.13-5.22 (2H, m), 4.48 (2H, br. s.), 4.08 (2H, br. s.), 3.44-3.58 (2H, m), 2.85 (3H, d, J=17.82 Hz), 1.21 (3H, d, J=7.03 Hz).

Workup

  1. customMeOH was removed under reduced pressure, to the residue Na2CO3 (aq, 100 mL) and EtOAc (250 mL)
  2. additionwere added
  3. stirringthe suspension was stirred vigorously for 10 min
  4. filtrationfiltered though glass frit, solid residue
  5. washwas washed with EtOAc (3×150 mL)
  6. washCombined EtOAc fractions were washed with std
  7. dry with materialNa2CO3 (aq, 2×100 mL), water (2×100 mL), brine (1×100 mL) and dried (Na2SO4)
  8. customEtOAc was removed under reduced pressure
  9. customthe residue was purified by flash chromatography (0-100% EtOAc/hexanes)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc718e382a4a4a099a153358183b3319
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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