Pyridine → HCID 131720628, compound

HRID 491380Notes

Reaction equation

HRID 491380 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[CH2:9]1[C:14](=[O:15])[N:13]([O:16][C:17](ON2C(=O)CCC2=O)=[O:18])[C:11](=[O:12])[CH2:10]1.N1C=CC=CC=1>C(#N)C>[OH:16][N:13]1[C:14](=[O:15])[CH2:9][CH2:10][C:11]1=[O:12].[C:17](=[O:16])([O-:18])[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 75103-PyridinemethanolHCID 676246Di(succinimido) carbonate

Product 1

HCID 131720628HCID 131720628, compoundYield 115.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.5 g (22.9 mmol) of 3-pyridylcarbinol in 100 mL of anhydrous acetonitrile was added 8.8 g (34.4 mmol) of N,N′-disuccinimidyl carbonate and 5.55 mL (68.7 mmol) of pyridine. The solution was stirred for 1 hour and then concentrated in vacuo. The residue was dissolved in ethyl acetate, then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated to afford 5.3 g of N-Hydroxysuccinimide-3-pyridylmethyl carbonate, mass spectrum m/e=251 (M+H), which was used directly in the next step without purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf08eda69577407aaa8fba69d0c0f2c7
Source dataset
uspto-grants-2009_05
Patent number
US07531538B2

Reaction notes

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