p-Toluenesulfonic acid → HCID 67843339, compound

HRID 1608668Notes

Reaction equation

HRID 1608668 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[C@H:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:10]([C:16]([OH:18])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:39]1[CH:44]=[CH:43][CH2:42][CH2:41][CH2:40]1>O1CCCC1.C(OCC)(=O)C>[C:1]([CH2:3][CH2:4][O:5][C:6]([C:8]1[C@H:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:10]([C:16]([O:18][CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44][O:39]2)=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 70340536HCID 70340536, compound

Product 1

HCID 67843339HCID 67843339, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 19 mg of (4R)-5-(2-cyanoethoxycarbonyl)-1,4-dihydro-2,6-dimethyl-4 -(3-nitrophenyl )pyridine-3-carboxylic acid in 0.5 ml of tetrahydrofuran were added 5 mg of p-toluenesulfonic acid, and then 0.138 ml of 3,4-dihydro-2H-pyran. The mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with 5 ml of ethyl acetate, washed with water, and dried over anhydrous Glauber's salt (sodium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified using preparative TLC to obtain 16.4 mg of the objective compound.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous Glauber's salt (sodium sulfate)
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-4b04d6c39a96401db5e3d7589cac9cf5
Source dataset
uspto-grants-1995_03
Patent number
US05395941

Reaction notes

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