HCID 59662197, compound → HCID 59662171, compound

HRID 409568Notes

Reaction equation

HRID 409568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([O:23][CH3:24])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O=[Pt]=O.CCO.CC(O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[C:21]([O:23][CH3:24])=[O:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 59662197HCID 59662197, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59662171HCID 59662171, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

Compound 4-3 (2.73 g, 7.76 mmol), EtOH/AcOH (1:1, 60 mL) and PtO2 (0.895 g) were shaken in a Parr apparatus (15 psig of hydrogen) for 10 hrs. The reaction mixture was filtered thru Celite®, washing with ethanol. The solution was concentrated, and the residue was diluted with dichloromethane and washed with saturated NaHCO3. The aqueous layer was again extracted with dichloromethane, and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The product was purified by flash chromatography (gradient elution with 15-50% ethylacetate (0.1% TEA) in heptane. The desired product Compound 4-4 was isolated as thick colorless oil (2.55 g, 93%). 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=2.3 Hz, 1H), 7.43 (d of d, J=8.5 and 2.3 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.22 (m, 2H), 3.91 (s, 3H), 3.52 (m, 1H), 2.82 (m, 2H), 2.8-1.5 (m, 4H), 1.48 (s, 9H); MS (ES+) m/z 253.8 (M-Boc+1); HRMS (FAB+) Calcd for C18H23ClNO4: 352.1316. Found: 352.1329.

Workup

  1. filtrationThe reaction mixture was filtered thru Celite®
  2. washwashing with ethanol
  3. concentrationThe solution was concentrated
  4. additionthe residue was diluted with dichloromethane
  5. washwashed with saturated NaHCO3
  6. extractionThe aqueous layer was again extracted with dichloromethane
  7. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by flash chromatography (
  11. washgradient elution with 15-50% ethylacetate (0.1% TEA) in heptane

Sources & evidence

ORD record
ord-8eb360cb90364207a0b5eff3770349df
Source dataset
uspto-grants-2014_06
Patent number
US08759342B2

Reaction notes

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