HCID 77230841, compound → HCID 77230840, compound

HRID 2203315Notes

Reaction equation

HRID 2203315 reaction equation
[CH3:1][CH:2]([C:7](=[O:12])[NH:8][CH2:9][C:10]#[CH:11])[C:3]([O:5][CH3:6])=[O:4]>CC#N>[CH3:11][C:10]1[O:12][C:7]([CH:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])=[N:8][CH:9]=1

Participants

3

Reactant 1

HCID 77230841HCID 77230841, compound

Product 1

HCID 77230840HCID 77230840, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

To the intermediate from Step A (1.46 g, 8.63 mmol) in 20 mL of CH3CN at room temperature was added a solution of AuCl3 (0.262 g, 0.863 mmol) in 5 mL of CH3CN. The resulting mixture was stirred at 50° C. for 14 hours and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product (pale yellow oil). 1H NMR (CDCl3, 500 MHz) δ 6.78 (1H, s), 4.07 (1H, q, J=7.4 Hz), 3.79 (3H, s), 2.37 (3H, s), 1.67 (3H, d, J=7.5 Hz).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography
  3. customto give the indicated product (pale yellow oil)

Sources & evidence

ORD record
ord-6efd6972b0c549bcbe5b9a385bddf6d3
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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