HCID 70084608, compound → HCID 22008782, compound

HRID 1602626Notes

Reaction equation

HRID 1602626 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC#N>[C:1]([O:5][C:6]([N:8]1[CH:13]=[CH:12][CH2:11][NH:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 70084608HCID 70084608, compound

Product 1

HCID 22008782HCID 22008782, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-2 (19.0 g, 63 mmol), Mg(ClO4)2 (2.8 g, 12.7 mmol), and CH3CN was heated at 50° C. for 2 hr. The cooled solution was diluted with CDCl3 and then washed with 1N HCl, sat. NaHCO3, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 75% EtOAc/hexanes→EtOAc) gave 5-3 as a brown solid.

Workup

  1. additionThe cooled solution was diluted with CDCl3
  2. washwashed with 1N HCl, sat. NaHCO3, and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7277701ca3df44d0a1bb8cfe260bb830
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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