Sodium Methoxide → HCID 67001978, compound

HRID 2279225Notes

Reaction equation

HRID 2279225 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:10]([CH2:23][C:24](OC)=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO.[Pt](=O)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:19]=3[NH:20][C:24](=[O:25])[CH2:23][CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 66769824HCID 66769824, compound

Product 1

HCID 67001978HCID 67001978, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×

Procedure

Platinum(IV) oxide (35 mg, 0.154 mmol) was added to a solution of the product of Example 51A (1.20 g, 2.92 mmol) in methanol (150 mL), and the suspension was stirred under hydrogen (1 atm) for 1 hour. The reaction flask was evacuated and purged with nitrogen (4 cycles), and the mixture was filtered through a pad of diatomaceous earth with a methanol (30 mL) rinse. A solution of 25% sodium methoxide in methanol (Aldrich, 1.83 g, 8.47 mmol) was added to the filtrate, and the solution was stirred at reflux under nitrogen for 41 hours and then cooled to room temperature. The reaction mixture was concentrated under vacuum, and the residue was purified by chromatography (SiO2, eluted with CH2Cl2—CH3OH, 95:5), followed by crystallization from ethanol (2 mL) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 2.15 (dd, J=13.7, 3.0 Hz, 1H), 2.22-2.32 (m, 1H), 2.31 (t, J=10.7 Hz, 1H), 2.75 (dd, J=13.7, 6.5 Hz, 1H), 2.83-2.96 (m, 2H), 3.23 (td, J=12.7, 2.8 Hz, 1H), 3.51-3.59 (m, 1H), 3.60 (s, 2H), 3.64-3.74 (m, 1H), 6.99 (dd, J=7.7, 5.0 Hz, 1H), 7.22-7.40 (m, 6H), 8.08 (dd, J=4.8, 1.6 Hz, 1H); MS (DCI) m/z 309 (M+H)+.

Workup

  1. customThe reaction flask was evacuated
  2. custompurged with nitrogen (4 cycles)
  3. filtrationthe mixture was filtered through a pad of diatomaceous earth with a methanol (30 mL)
  4. washrinse
  5. stirringthe solution was stirred
  6. temperatureat reflux under nitrogen for 41 hours
  7. concentrationThe reaction mixture was concentrated under vacuum
  8. customthe residue was purified by chromatography (SiO2, eluted with CH2Cl2—CH3OH, 95:5)
  9. customfollowed by crystallization from ethanol (2 mL)

Sources & evidence

ORD record
ord-778fd25961ab4eccb190f4984434e4f6
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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