Ethyl nipecotate → HCID 136403364, compound

HRID 1534966Notes

Reaction equation

HRID 1534966 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.[CH2:25]([O:27][C:28](=[O:35])[CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1)[CH3:26]>CS(C)=O>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([N:31]3[CH2:32][CH2:33][CH2:34][CH:29]([C:28]([O:27][CH2:25][CH3:26])=[O:35])[CH2:30]3)=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

4

Reactant 2

HCID 98969Ethyl nipecotateHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 136403364HCID 136403364, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) was placed into a 10 ml round bottom flask with 2 ml dry dimethylsulfoxide and a magnetic stirring bar. 150 mg of (+ -)-ethylnipecotate was added to the solution. The solution immediately turned green and was stirred at room temperature (25°) for two hours. The dimethylsulfoxide was removed under reduced pressure with gentle heating. 10 ml of ether was added to the yellow residue and the solid was broken up with a spatula. The solution was stirred until a fine white homogeneous precipitate was obtained. The solution was filtered and the solid washed with ether to yield 285 mg of 1-[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]-3-piperidinecarboxylic acid, ethyl ester (AIT-0103) as a white solid. Yield: 90%. m.p.: 171°-175°.

Workup

  1. customThe dimethylsulfoxide was removed under reduced pressure with gentle heating
  2. addition10 ml of ether was added to the yellow residue
  3. stirringThe solution was stirred until a fine white homogeneous precipitate
  4. customwas obtained
  5. filtrationThe solution was filtered
  6. washthe solid washed with ether

Sources & evidence

ORD record
ord-957bfe93958244fc9700ae1cd5529995
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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