Sodium Hydroxide → HCID 117720296, compound

HRID 530249Notes

Reaction equation

HRID 530249 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:21])[CH3:20])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Na+]>C(O)(=O)C.ClCCl.[Pt](=O)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:20])[CH3:21])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 117720150HCID 117720150, compound

Product 1

HCID 117720296HCID 117720296, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 13a (178 mg, 0.63 mmol) in acetic acid (2 mL) was added platinum dioxide (25 mg) and the reaction was stirred at room temperature under an atmosphere of hydrogen for 4 hours. The mixture was diluted with dichloromethane (40 mL) and basified with 1 N NaOH (35 mL) and the organic phase was separated. The aqueous layer was extracted with dichloromethane (30 mL). The combined organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1) to afford the title compound as a dark brown oil (130 mg, Yield: 72%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.4 Hz, 1H), 7.73 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.2 Hz, 2H), 3.01 (t, J=6.2 Hz, 2H), 2.11-2.02 (m, 1H), 1.81-1.77 (m, 1H), 1.61-1.54 (m, 2H), 1.44-1.41 (m, 1H), 1.34-1.24 (m, 3H), 1.10-0.98 (m, 4H), 0.77 (s, 3H), 0.74 (d, J=6.4 Hz, 3H) ppm; Mass spectrum (ESI +ve) m/z 286 (M+H+).

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1)

Sources & evidence

ORD record
ord-6ada8abf14f24b41a75d600a059cca76
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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