Pyridine → HCID 69955438, compound

HRID 2293305Notes

Reaction equation

HRID 2293305 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]2[CH:14]([CH3:25])[NH:15][CH:16]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:10]2[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(#N)C>[C:33]([N:15]1[CH:14]([CH3:25])[CH:11]2[CH:10]([C:9](=[O:26])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:12]2=[O:13])[CH:16]1[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69955228HCID 69955228, compound

Product 1

HCID 69955438HCID 69955438, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.B)c) A solution of 3.46 g (10 mmol) of (1RS,3SR,3aRS,6aSR)-4-(5-benzyl-3-methyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile in acetonitrile (10 ml) was treated with pyridine (20 mmol). Acetic anhydride (20 mmol) was slowly added dropwise while cooling with ice. The cooling was removed and the reaction mixture was stirred for a further 1.5 hours. Thereafter, the reaction mixture was poured into saturated NaCl solution and extracted with dichloromethane. The solvent was removed and the residue was separated chromatographically (hexane:ethyl acetate=1:1). (1RS,3SR,3aRS,6aSR)-4-(2-Acetyl-5-benzyl-3-methyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile (83%) was isolated as a colourless solid. M.p.: 107°-109° C. EI-MS: 387 ([M]+, 72); 344 (35); 320 (28); 254 (18); 183 (16); 169 (17); 158 (53); 91 (86); 43 (100).

Workup

  1. temperaturewhile cooling with ice
  2. customThe cooling was removed
  3. additionThereafter, the reaction mixture was poured into saturated NaCl solution
  4. extractionextracted with dichloromethane
  5. customThe solvent was removed
  6. customthe residue was separated chromatographically (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1781dea6e52d44ac95bf9667f576c0a5
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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