HCID 57942715, compound → HCID 57942825, compound

HRID 1438121Notes

Reaction equation

HRID 1438121 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]1[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:18]=[CH:19][CH:20]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2]>C(O)C.Cl.[Pt]=O>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[C:8]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH:9]=1

Participants

5

Reactant 1

HCID 57942715HCID 57942715, compound

Product 1

HCID 57942825HCID 57942825, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To platinum oxide (0.5 g) was added 19C in ethanol and hydrogen chloride (0.45 mL) under nitrogen. The reaction was placed under hydrogen (40 psi). After 1.5 h the reaction was half done, platinum oxide (200 mg) was added and reaction was stirred under hydrogen (40 psi) for 2 h. The catalyst was filtered over celite and washed with ethanol. The filtrate was neutralized with diethylamine. The solvent was evaporated and the crude residue was redissolved in dichloromethane. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed and the crude product was purified by flash column chromatography to give a white solid product 23E (1.6 g, 88%). 1H NMR (400 MHz, Methanol-d4) δ ppm 1.24 (m, 15H) 1.84 (m, 3H) 2.37 (m, 1H) 3.15 (m, 1H) 3.62 (m, 2H) 5.28 (s, 1H) 6.53 (d, J=19.56 Hz, 2H) 7.50 (d, J=8.56 Hz, 1H).

Workup

  1. customreaction
  2. filtrationThe catalyst was filtered over celite
  3. washwashed with ethanol
  4. customThe solvent was evaporated
  5. dissolutionthe crude residue was redissolved in dichloromethane
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed
  9. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-5ec5dfedea39467d833bad523fd21d78
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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