HCID 86634823, compound → HCID 68921165, compound

HRID 1808138Notes

Reaction equation

HRID 1808138 reaction equation
[C:1](=[O:25])([O:3][C@H:4]([CH:11]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:5](=[O:10])[NH:6][CH2:7][C:8]#[CH:9])[NH2:2]>C(#N)C.[Au](Cl)(Cl)Cl>[C:1](=[O:25])([O:3][C@@H:4]([C:5]1[O:10][C:8]([CH3:9])=[CH:7][N:6]=1)[CH:11]([C:21]([CH3:22])([CH3:24])[CH3:23])[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[NH2:2]

Participants

4

Reactant 1

HCID 86634823HCID 86634823, compound

Product 1

HCID 68921165HCID 68921165, compound

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-tert-butyl-3-(1H-indol-3-yl)-1-oxo-1-(prop-2-ynylamino)propan-2-yl carbamate (2.20 g, 6.44 mmol) in acetonitrile (25 mL) was mixed with gold(III) chloride (190 mg, 0.63 mmol) at room temperature and stirred for 18 h at 50° C. The solvent was removed in a vacuum and the residue was purified by flash chromatography (60 g, 15×4 cm) with ethyl acetate/cyclohexane (1:1).

Workup

  1. customThe solvent was removed in a vacuum
  2. customthe residue was purified by flash chromatography (60 g, 15×4 cm) with ethyl acetate/cyclohexane (1:1)

Sources & evidence

ORD record
ord-cea0f22bdf5e41d0a4db9d782e1d6a4e
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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